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Патент USA US3037990

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3,037,980
‘ United States Patent 0 M vC6
Patented June 5, 1962
1
2
sponding mercapto compounds of the formula:
3,037,980
PYRROLOPYRIMIDINE VASODILATORS AND
METHOD OF MAKING THEM
George H. Hitchings, Yonkers, Kurt W. Ledig, New Ro
chelle, and Robert A. West, White Plains, N.Y., as
signors to Burroughs Wellcome & Co. (U.S.A.) Inc.,
Tuckahoe, N.Y., a corporation of New York
No Drawing. Filed Mar. 4, 1960, Ser. No. 12,675
Claims priority, application Great Britain Aug. 18, 1955
1 Claims. (Cl. 260—-256.4)
10
The present application relates to a new group of
N
The compounds having R1 as a hydrogen atom may
pyrrolo(2,3~d)py1imidines bearing amino groups in the
also be prepared from the corresponding 5-(2,2-dialkoxy
4-position of the pyrrolo(2,3-d)pyrimidine ring system
ethyl) -6-aminopyrimidines
and is a continuation in part of our US. applications
Serial No. 602,912, ?led August 8, 1956 and 721,104, 15
Ra
?led March 13, 1958. The new derivatives may be rep
R4
20
23R.
RAM/k1
'
34
\N/
N l
resented by the following formula:
N/
'
.1\N
NH:
by closure of the pyrrole ring with elimination of two
25
1
molecules of alkanol.
The following examples illustrate the methods used in
the preparation of the new substances.
R1
EXAMPLE 1
wherein R1 and R2 are selected from the class consisting
4-n-Pr0pylamin0pyrr0l0 (2,3-d )Pyrimidine
of hydrogen and lower alkyl groups, R3 is selected from 30
the class consisting of hydrogen and lower alkyl groups,
To 1.3 grams of 4-chloropyrrolo(2,3-d)pyrimidine
‘R; is selected from the class consisting of alkyl, aralkyl,
(0.0085 mole) in 30 ml. of absolute ethanol containing
alkoxyalkyl, dialkoxyalkyl, dialkylaminoalkyl and hy
one drop of concentrated hydrochloric acid was added
droxyalkyl, and R3 andlR4 together form a piperazino
2.5 ml. of n-propylamine (0.02 mole). The solution
ring, R3 and R4 together containing a maximum of ten 35 was heated in a metal bomb at 125° C. for 7 hours. The
carbon atoms.
>
bomb was cooled and its contents were evaporated to
dryness on the steam bath. The residual thick oil was
cological activities, in particular for their hypotensive
triturated with 5 cc. of 2.5% sodium hydroxide and al
effects. They also have muscle relaxant, hypnotic and
lowed to stand at room temperature until crystallization
anticonvulsant activities. In hypotensive activity they 40 occurred. Thus, 1.2 grams of crude product was ob
are quite potent and show activities at small fractions
tained by ?ltration. This was recrystallized from aque
The new derivatives are useful for their pharma
of the toxic doses which lie in the neighborhood of 100
mg./kg. Doses in the range of 0.5 to 4 mg./kg. produce
falls in systolic blood pressure of dogs of from 5 to
ous ethanol (30%) with added Darco. The compound
melted at 162° C.
EXAMPLE 2
45 mm. of mercury, lasting up to 1.5 hours. These ef 45
fects appear to be produced or at any rate accompanied
by peripheral vasodilation. Coronary vasodilation is also
a prominent feature of their effects.
A number of ap
plications of these ?ndings will be apparent to those versed
2-Methyl-4-n-A mylaminopyrrolo (2,3-d) Pyrimidine
A solution of ethyl a(2,2-diethoxyethyl)cyanoacetate
(11.4 g.) in 25 ml. of ethanol was mixed with a solu
tion of acetamidine (from 4.3 g. of acetamidine hydro
in the art.
50 chloride and 1.15 g. sodium metal in 25 m1. ethanol) and
The new substances are formed by the reaction of a
the resultant solution was heated at re?ux temperature
4 - chloropyrrolo(2,3 - d)pyrimidine with an appropriate
amine to give the 4-amino derivative:
(in
N/
Ra
l \R.
for 6 hours. The 4-amino-5-diethoxyethyl-6-hydroxy-2
methylpyrimidine was recovered by evaporation of the
solvent, addition of aqueous acetic acid to pH 5.0 and
55 ?ltration.
The product was dissolved in 100 ml. of 95% alcohol,
2 ml. of concentrated sulfuric acid were added and the
solution was heated under re?ux for 6 hours. The mix
ture was chilled and ‘the 4-hydroxy-2-methylpyrrolo~
60 (2,3-d) pyrimidine was recovered by ?ltration.
To 0.9
pyrimidine
containing
was added
grams of 2-methyl-4-chloropyrrolo(2,3-d)
(0.0054 mole) in 25 ml. of absolute ethanol
one drop of concentrated hydrochloric acid
2.4 ml. of n-amylamine (0.016 mole). The
wherein R1, R2, R3 and R4 have the values assigned above. 65 solution was heated at 140° C. for 7 hours in a metal
bomb. The bomb was cooled and its contents evapoe
602,912 and two additional intermediates 7-methy1-, and , rated to a thick oil on the steam bath. The oil crystal-'
The 4-chloro derivatives are described in US. application
2-methyl-4-chloropyrrolo(2,3-d)pyrimidine are described
lized upon trituration with 5 cc. of 2.5% sodium hydrox
herein. The 4-chloropyrrolo(2,3-d)pyrimidines~ are the
ide and yielded 1.1 grams of product after ?ltering and
subject of a divisional application of these applicants.
70 drying over calcium chloride in a dessicator. The prod
The compounds having R2 as a hydrogen atom may
uct was recrystallized from 25% aqueous ethanol with
also be prepared by catalytic dethiolation of the corre
added Darco with melting point of 157-159" C
3,037,980
'
‘
3
.EXAMPLE 3
_
Example:
.
.
no)-pyrrolo(2,3-d)pyrimidine ....... __
144-146
27. 4 - (3 - methoxypropylamino)pyrrolo
After cooling to 15°’ C., 0.95 grams '
(2,3-d)pyri=midine ,_'..__,____,_ _______ _1 144-145
of NaH (0.038 mole) was added. The reaction mixture
.28. 4]- dimethylaminopyrrolo(2,3 - d)py-
was allowed to sit at room temperature ‘(under anhydrous
conditions) until no further H2 gas was liberated (about 10
6-7 hours). The clear solution was cooled to 5° C.
' rimidine
,
’__; ___________ _'_ ______ __'__
222
29. 4 '- methylethylarninopyrrolo(2,3'- d)-
'
and 6.2 grams (0.043 mole) of (H31 was added. The
'
pyrimidine‘ r....i____'_, __________ __'__‘___
1,70
30. 4 - inethyl - n’,- propylaminopyrrolo?,
' reaction ?ask was sealed and allowed to stand at room
3-d)pyrimidine
temperature for 24 hours, following which it was heated
'
_.___'____.' __________ __ 148-149
31. 4 - methylisopropylaminopyrrolo(2,3
at 45° C. ,for 3-4 hours. Thesuspension was diluted 15
‘
d)pyrimidine
' with ‘an equal volume of water, chilled, allowed to stand
_____ .._‘____' ________ __;_
156-157
32. 4 - diethylaminopyrrolo(2,3 -- d)pyrimi- -
overnight and ?ltered to yield 4.1 grams of desired prod
uct melting at 130° C. (75% yield)."
To 1‘ g.v of 4-chloro-7-methylpyrrolo(2,3-d)pyrimidine
', in 25 mlJof ethanol (absolute) were added 1 drop of 20
concentrated hydrochloric acid and 1.5 ml. of n-arnyl
dine
~
7
'
174-175
33. i4 - di - n - propylaminopyrrolo(2,3-d),-
pyrimidine
‘
;, ______ __‘____,__....__,____
‘
34. 4 - piperidinopyrrolo(2,3'- d)-pyrirni-
118
,
dine, melting to a clear oil at ________ __ 184-185
amine. .The solution was heated in a bomb at 130° C.
1* crystallized from hep‘tane.
for 6 hours. 'After, cooling, the contents of the bomb »
were evaporated to dryness and ‘the solid ‘was tritur'aited
'
1’ crystallized from benzene-heptane as in Example ‘3.
c ‘Crystallized from benzene.
with sodium hydroxide. 'I‘hey'recrystallized by solution
in hot ‘benzene followed by the addition of hexane to a 275
permanent turbidity.‘ On chilling the material’ Crystal
lined and was recovered by ?ltration. It melted at 125;
' 127° C.
M.P. f’ C.
(2,3-d)pyrimidine *1 _______________ __ 167-168
(0.033 mole) was dissolved in 40 m1. of NaH-dried di
7
‘
26. 2 - methyl - 4-1 (2 -. methoxyethylami
eight-tenths grams of 4-chloropyrrolo(2,3-d)pyrimidine
methylformamide.
7
25. 4 - (2 - methoxyethylamino)pyrrolo
4-n-Amylamin0-7-Methylpyrr0l0(2,3-d)Pyrimidine
7-me'thyla4-chloropyrrolo (2,3-d)pyrimidine.—-Five and
I
' EXAMPLE 35
4-n-Nonylaminopyrrolo(2,3-d)Pyrimidine
4-ch-loropyrro1o(2,3-d)pyrimidine (1.2 g.) and n-non
' ylamine (5 g.) were re?uxed in water (50 ml.) for 2
a
By the method’ of Example 1, the following additional 30 hours. The mixture was treated with 5% aqueous so
dium hydroxide (4 ml.), chilled for two hours, and ?l
itereda After dryingrin the dessicator, the solid (2.55
MP.” C.
pyrrolo(2,3-d)-pyrimidines have ibeen prepared: V
Example:
'
p
4
'
'
‘
'
.
. vg.) was recrystallized from hot aqueousethanol yielding
'
4-n-nonylaminopyrrolo(2,3-d)pyrimidine (2 g.), melting
~ 4. 4 - methylaminopyrrolo (2,3 - d)
pyrimidine __; ____________________ __
236
35
5. 4 - dimethylaminopyrrolo(2,3 - d)py
rimidine
_______________________ __,._
point 122-124° C., as a hemihydrate.
EXAMPLE 36
222
2-Methyl-4-Benzylaminopyrlfolo(2,3-a')Pyrimidine
6. 4 - ethylaminopyrrolo(2,3, - d)pyrirni
idine
205
7. 4 - ethyhnethylaminopyrrolo(~2,3 - d)
'
pyrimidine
2 - methyl - 4 - chloropyrrolo(2,3t - d) pyrimidine (1.0
40 g.) and henzylamine (4.0 g.) were re?uxed in water
___; _________ -1 ______ __-_
170
'8. 4 - n - amylaminopyrrolo(2,3 -‘ d)pyrimidine
V
(50 ml.) for 3 hours. Ethanol was slowly added, while
,
_______________ _,_ _______ __
129
e
heating, until complete solution was attained. The so
\ lution was chilled overnight and 2-methyl-4-benzylamino
9. 4 - iso - propylaminopyrrolo(2,3 - d)
pyrimidine
pyrrolo(2,3-d)pyrimidine (1.4g), melting point 205
____ -2 ________________ __ ‘169-170
' 10. 4 - methylpropylaminopyrrolo(2,3-d)-'
pyrimidine
207° C., was ?ltered off.
1
______________________ __ 148-149
11. 4, -hydroxyethylaminopyrrolo(2,3 - d)vpyrimidine ______________ _.>. _______ __
.
.
'
Z-Meihyl-4-N'-Methylpiperazin0pyrrolo(2,3
'
‘209
.
12- 4 - diethoxyethylaminopyrro1o(2,3 - d)
145-146
rirnidine
________________________ .__
.15. 4 - sec - buty1aminopyrrolo(2,3
173-174
- d)- _
.
.
rimidine ° ____ __,_; _______________ _'_
I83
17. 4 - iso - amylarninopyrro1o(2,3 - d)-
I i I
pyrimidine“-.. ______ __'_.___; ______ .._ 166-167
18. '4'- sec - arnylaminopyrrolo(2,3 - d)'
20. 4 -n - heptylaminopyrrolo(2,3 - d)
pyrimidinea _____________________ _.. 126-127
21. 4
- n
-
octylaminopyrrolo(2,3
' pyrimidine”
22. 4 - n
-
-
d)
__'___' ______ __' _______ __
ally1aminopyrrolo(2,3
-,d)-
118-119
,
,
pyrimidine _____ _-_ __________ __‘_.__.___
23. 4 - diethylaminoethylaminopyrrolo(2,r
3-d)pyrimidine
__' ____ _, ______ __V____
24. 4 - cyclopentylaminopyrrolo(2,3 .-'d), pyrimidine
w _'
tained by slowly evaporating off one-half of the mother
liquor.
Recrystallization from. n-heptane yielded a hemi
hydraite, melting point 19l-192° C.
60
EXAMPLE 38
'
4-N'-Erhylpiperazin0pyrr0l0(2,3-d) Pyrimidine
4~chloropyrrolo(2,3-d)pyrimidine (1.2 g.) and N-eth
-
pyrimidinea ___________ __'__; _____ __ 150-151
v
g.)
idine as a. dihydrate. A second crop (0.35 g.) was ob
“
pyrimidine ____' ___________________ __ 140-141
d)-
(2.0
vchilled overnight yielding a primary crop (2 g.) of 2
pyrimidine° ____________ _.;_'_ ______ __ 125-126
-
d)Pyrimidine
55 methyl - 4 - N’ - methylpiperazinopyrrolo(2,3 - d)pyrim,
16. tert - hutylaminopyrrolo(2,3 - d) - py
19. 4 - n - hexylaminopyrrolo(2,3
‘
i was added and when dissolved the clear solution was
14. 4 - isobutylaminopyrr0lo(2,3 - d) - py
,
'
and N-amethylpiperazine (5.0 g.) rwerere?uxed in water
(65 ml.) for 2 hours. Then potassium hydroxide (3 g.)
'
pyrimidine _______ _; ______ __' ______ __
V
’ 2-methyl-4-ch1oropyrro1o(2,3-d)pyrimidine
pyrimidineb ____________________ __“_ 124-126.
13. 4 -' no - butylarninopyrrolo(2,3. e d)-
'
EXAMPLE 37
167
.
146-147
-
________ __-____...._.._'-_.__._. 162-16
65 ylpiperazine (4 g.) were heated in water (50 ml.) at
85-90" C. ‘for 2 hours. Then potassium hydroxide (3.5
g.) was dissolved in the reaction mixture and the solu
tion was chilled overnight. Upon ?ltration 4-N'-ethy1
.rpiperazinopyrrolm2,3-d)pyrimidine (1.5 g.) was ob
70 rained as a dihydrate. Drying for 1.5 hours at 135° C.
gave a hemihydrate. The compound changed in crys
italline form at 150-160“ C. and melted toya clear oil
a at 175? 0.
_ The following compounds were prepared, from the
75 appropriate amine and a 4-chloropyrrolo(2,3-d)'pyrirni
3,037,980
5
6
dine by methods similarto those described in Examples
'The following compounds were prepared from ammo
nia and the appropriate 4-chloropyrrolo(2,3-d)pyrimidine
35 to 38.
° C.
by methods similar to that described in’ Example 64.
39. 4 - n - hexylaminopyrrolo(2,3-d)pyrimi
dinea
.
150-151
dine
-
____
129-130
dine a
135
42. 4 - n - octylaminopyrrolo(2,3 - d)pyrimi
10
dine a
118-119
______________________ __ 126-138
44. 4 - n - decylaminopyrrolo(2,3 - d)pyrimi
dine
_
110-111
45. 4 - cyclohexylaminopyrrolo(2,3 - d)pyrirni
dine
in water (60 ml.) at pH 2.0 by the addition of a 1:1
dilution of hydrochloric acid. A small amount of black
15 tar was ?ltered o? and the ?ltrate was adjusted to pH
10.0 to give 4-pyrrolidinopyrrolo(2,3-d)pyrimidine (1.7
149-151
g.) melting point 263-265 ° C., as a white amorphous
4 - benzylaminopyrrolo(2,3 - d)pyrimi
dine
precipitate.
196
47. 2 _- methyl - 4 - p - methylbenzylaminopyr
20
rolo(2,3-d)pyrimidine __________________ __.
197-198
The hydrochloride melted at __________ __ 231-234
49. 4 ~ (2 - dimethylaminoethylamino)pyrrolo
25
(2,3-d)pyrimidine
_____________________ _ . 164-165
50. 4 - (2 - diethylaminoethylamino)pyrrolo.
(2,3-d)pyrimidine ____________________ __ 146-147
51. 4 - (2 - hydroxyethylamin'o)pyri'o1o(2,3.
d)pyrimidine
________________________ __
. 209
30
52. 4 -. (2,2 - diethoxyethylamino)pyrrolo(2,3
pyrrolo(2,3-d)pyrimidine
_l_ ___________ __
.
pyrimidine
35
55. 4 - carboxymethylaminopyrrolo(2,3-d)py
154
____________________ __ 228-230
________________________ __ 205-206
79. 4 - (p - methoxybenzylamino)pyrrolo(2,3
________________________ .__ 236-239
80. 4 - methyl - n - nonylaminopyrrolo(2,3
d)pyrimidine ________________________ __ 105-106
81. 4 - m - methylbenzylaminopyrrolo(2,3
57. 4 - methyl(2,2 - diethoxyethyl)aminopyr
________________ __ 127-129
5 8. 2 - methyl - 4 - methyl(2,2 - diethoxyethyl)
d)pyrimidine
________________________ __.
155
82. 4 - o - methylbenzylaminopyrrolo(2,3 -d)
87-89
83. 4 - (2’ - pyridyl)methylaminopyrrolo(2,3
aminopyrrolo(2,3-d)pyrimidine _________ __
pyrimidine
59. 4 - methyl(3.3 - diethoxypropyDaminopyr
- ethylcarboxymethylaminopyrrolo(2,3
d)pyrimidine
________________________ __
204
61. 4 - morpholinopyrrolo(2,3 - d)pyrirnidine__
215
50
178-180
259-261
________________________ __
184-186
84. 4 - diethanolaminopyn-olo(2,3 - d)-pyrimi
dine
“ Crystallized from heptane.
b Crystallized from benzene-heptane as in Example 3.
__ 196-198
85. 2 - n - propyl - 4 - n - nonylaminopyrrolo
(2,3 -d) pyrimidine ____________________ ._ _
86. 7 - methyl 4 - n - nonylaminopyrrolo(2,
3-d)pyrimidine hydrochloride ___________ __
The following compounds weer prepared from the
appropriate amine and a 4-chloropyrrolo(2,3-d)pyrimi
dine by methods similar to those described in Exam
ples 1 to 3.
63. 4 - ethylamino - 7 - methylpyrrolo(2,3~d)
129-130
(2,3-d)pyrimidine
____________________ __
147-148
88. 4 - (4' '- methylpiperazino) - 7 - methyl
pyrrolo(2,3-d)pyrimidine hydrochloride, etler
62. 2 - methyl - 4 - ethylaminopyrrolo(2,3-d)
189-190
94-96
87. 2,7 - dimethyl - 4 - benzylaminopyrrolo
° C.
pyrimidine
____ __. __________ __;_‘_'__‘_'____- 203-205
d)pyrimidine
dine
pyrimidine
pyrimidine
d)pyrimidine
40
56. 4 - fur-furylaminopyrrolo(2,3 - d)pyrimi
d)-pyrimidine
272-276
>
78. 4 - (p - chorobenzylamino)pyrrolo(2,3
evolution of gas.
60. 4
184-185
230-236
__________________________ __ 220-222
(2,3-d)pyrimidine
rimidine, which turned pink at 230° C., and
decomposed completely at 265-270° C. with
rolo(2,3-d)pyrimidine _________________ _..
216-217
77. 4 - N - methyl - N - benzylaminopyrrolo
______________________ __ 120-1211
rol'o(2,3-d)pyrimidine
'
215-216
76. 4 - p - methylbenzylaminopyrrolo(2,3-d)
129-130
54. 4 - (3,3 - diethoxypropylamino)pyrrolo-(2,
3-d)pyrimidine
71. 2 - methyl - 4 - (2’ - pyridylmethyl)amino~
pyrrolo(2,3-d)pyrimidine __l_-_'________ __
72. 2 - methyl - 4 - (3’,4',5'-trimethoxybenzy1)
aminopyrrolo(2,3-d)pyrimidine _; ________ __
73. 2 - methyl - 4 - (3' - methylbenzyl) amino
pyrrolo(2,3 - d)pyrirnidine base ________ .__
Hydrochloride salt ____..'______________ __.
74. 4 - (2' - thenylamino) - pyrrolo(2,3 - d)
pyrirnidine
'
O C.
75. 4 - (o - chlorobenzylamino)pyrrolo(2,3-d)
d)pyrimidineb _______________________ __ 124-126
53. 2 - methyl - 4 - (2,2 - diethoxyethylamino)-
.
70. 2 - methyl - 4 - (3' - methoxy)propyl‘
aminopyrro'lo(2,3-d)pyrimidine _________ _._ 188-189
211
48. 4 - (2 - phenylethylamino)pyrrolo(2,3-d)
pyrimidine
A solution of 4-chloropyrrolo(2,3-d)pyrimidine (1.7
g.) and pyrrolidine (3 g.) in 95% ethanol (35 ml.) was
heated in a bomb at 130° C. for 6.5 hours. The sol
vent was evaporated and the oily residue was dissolved
43. 2 - phenyl - 4 - n - nonylaminopyrrolo(2,
46.
° C.
EXAMPLE 69‘
41. 4 - n - heptylaminopyrrolo(2,3 - d)pyrimi
3-d)pyrimidine
>
68. 2 - methyl - 4 - aminopyrrolo(2,3 - d)py-v
rimidine
‘
290-295
40. 4 - isohexylaminopyrrolo(2,3 - d)pyrirni
60
159
vescence at 190-210° C.; residue melts at
233-238° C.
89. 2 - n - propyl - 4 - benzylaminopyrrolo
64. 4 - methyl - n - amylaminopyrrolo(2,3,d)
pyrimidine __________________________ __ 133-135
(2,3-d)pyrimidine ____________________ __ 161-162
90. 2 - n - propyl - 4 - (4' - ethylpiperazino)
The following compounds were prepared from the
appropriate amine and a 4-ch‘loropyrrolo(2,3-d)pyrimi
dine by methods similar to those described in examples
91. 4 - (4' - isopropyl)piperazinopyrrolo(2,
35 to 38.
92. 4 - (4' - n - propyl)piperazinopyrrolo(2,
pyrrolo(2,3-d)pyrimidine
3~d)pyrimidine
° C.
65. 2 - methyl 4 - n - nonylaminopyrrolo(2,3
d)pyrimidine
3—d)pyrimidine
70
________________________ __ 110-113
66. 2 - methyl - 4 - (2 - phenylethylamino)pyr
121
______________________ __ 178-179
________ __. _____________ _._
172-174
93. 4 - 4’ - oarbethoxy)piperazinopyrro'lo(2,
3-d)pyrimidine
_______________ _. _______ __
204-205
94. 4 - (4' - ,8 - hydroxyethyDpiperazinopyr
rolo(2,3-d)pyn'midine _________________ __ 208-209
67. 4 - N’ - methylpiperazinopyrrolo(2,3-d)py
rimidine
_________ __v_____
rolo(2,3-d)pyrimidine _________________ __
176-177
95. 4 - (4’ - n - v‘butyl)pipe1'azinopyrrolo(2,
142 75
3-d)pyrirn-idine _______________________ __ 171-172
53,037,980
7
.
.. .
7
1. A compound of the formula:
Q c.
' 96. 4 - (33435’ - trimethybpiperazinopyrrolm
(La-ammonia ____________________ __‘ 206.201‘
_
97. 4 - (4’ - ethyl)piperazinopyrrolo(2,3-d)
.
N
I \R4
pyrimidinefmethiodidenn; _______ __"‘_____ 225-230
198. 4 - n - octy1oxy-pyrro1o(.2,3-d)pyrimidine__ 107-109
99. 4 - n - octylmercaptopyrrolo(2,3-d)-py
v
rimidine
_
_
111-112
100. 2- - methyl - '4 - v(/8 - dirnethylaminoethoxy
pyrrolo(2,3-d)pyr_imidine methiodide _____ __ 201-203 10
101. 2 - methyl - 4 - (p - methoxybenzylamino) pynolo(2,3_-d)pyri-midine
________ -1 ____ __
189-191
102. -2 ~ methyl - 4 - (3' - isopropoxy) - n - pro
'
py1aminopyrrolo(2,3-d)pyrimidine
_______ __
wherein R1 and R2 are selected from the class consisting
139-140
'
15
103. 2 ' methyl - 4 - methyl - n - propylamino
pyrrolo(2,3-.d) pyrimidine ______________ __ 123-125
104. 2 - methylpyrrolo(2,3 -’d)pyrimidine____ 179-180
105. 2 ~mcthyl - 4 - (4’ - n - propylpiperazinol.
I’ pyrrolo(2,3-d)pyrimidine
__________ __.____
194-196
106. 2 - methyl .- 4 - (B -. phenyhethylamino- _
' '
~
of hydrogen and lower alkyl groups, R3 is selected from
the class consisting of hydrogen and lower alkyl groups,
R; is selected fromrthe?classrconsi-sting of alkyl,_phenyl~
alkyl, alkoxyalkyl, dialkoxyalkyl, dialkylaminoalkyl and
hydroxyalkyl, and R3 and Rétogether form a piperazino
20 ring, R3 and R4 together containing a maximum _of ten
carbon
_‘ pyrrolo(2_,p3p~d)pyrimidine base "I ________ __ 208-209
Hydrochloride salt __________ _; ______ .. 112-116
'107. 2 - methyl - 4 -7 (p - chlorobenzy1amino)
pyrrold(2,3-d)pyrimidine -. _______ __>_____ 234-235
108. 2 '- methyllf 4 - (N - methylbenzylamino)-
25
2.
3.
4.
5.
atoms.
..
rimidine.
pyr-roltr(2,'3-d)pyritrlidincv ______________ __ 218-219
109. 2.- methyl - 4 - (2’ - thenylamino)pyr
111. 2 - methyl - 4 - (or. - furfurylamino)-pyr—
rolo(2,3-d)pyrimidine (change in crystalline .
form above 160° C.) ________________ _V___ 195-197
What we claim is:
.
'
'
’
,
‘
.
.
.
.
.
'
6. 2-methyl-4~(2'-methoxyethyl)amjnopyrrolo(2,3-d)a
pyrimidine.
trolo(2,3—d)pyrimidine ____ __V_________ _.._.. 214-215
110. 2 - methyl ‘- >4 -‘ (o - chlorobenzylamino)
pyrrolo(2,3-d)pyrilmidine _________ _>_____'_ ‘219-222 30
.
4-‘(methyl-n-propylamino)pyrrol0(2,3-d)pyrimidine.
2-methyl-4-benzylaminopyrro1o(2,3-d)pyrimidine.
4-n-nonylaminopyrrolo(2,3-d)pyrimidine.
2-methyl-4-(4’-methy1piperazino)pyrrolo(2,3-d)py
.
.
"
7. 4-diethoxyethylaminopyrrolo(2,3-cl)pyrimidine.
8. 4-ethy1aminopyrrolo(2,3-d)pyrim.idine.
9. 4-n-propy1aminopyrrolo(2,3-d)pyrimidine.
' 10. '4-methoxymethylaminopyrro1o(2,3-d)pyrimidine.
11. 4-tert-hutylaminopyrrolo(2,3-d)pyrimidine. »
No references cited.
n.oe;m
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