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Патент USA US2403713

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Patented July 9, i946
7:15;.1?
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.v"UNITE-oz..s'rAfrEs PATENT;- OFFICE _ V
PREPARATION of‘ 4.-BA,s'roKilIlii"sUBsT1-; . I .
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TUTED
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'2-SULPHANILAMIDQPYRIML,»
DINES
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Jackson P.-English, Stamford, Conn, assignor to
American Cyanamid Company, New York,
N. Y., a corporation of Maine
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No Drawing. Application July 17, 1944,
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Serial No.'545,395
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6 Claims.
(Cl. 260—239.6)
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This invention relates to the preparation of
sulphanilamido pyrimidines. . More particularly
it relates to the preparation of 2-sulphani1amido4-aminopyrimidines.
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V
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2,
.
with or without a solvent at a temperature
of about 50° C. to about 200° C. for from
about one-half hour to about four hours depend-'
.
ing on the temperature used.
The crude reac
I have discovered that when 2-sulphanilamido- 5 tion product may be isolated and, puri?ed by ex
4-alkoxypyrimidines are heated with ammonia I traction with dilute alkali,.?ltration and precipi
or amines having a, reactive hydrogen, reaction
tation from the alkaline solution by neutraliza
occurs resulting in the formation of 2‘-sulphanil- ' tion. The crude product may also be puri?ed by
amido-4-(amino or substituted amino) pyrimisuspendingit in water, ?ltering and recrystalliz
dines having the following structural formula:
X
7
“
N/
\
\
.
N
/
10 ing from aqueous solution.
.
.
>
Y
‘ '
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My invention will now be illustrated in greater
detail by means of the following speci?c examples, . V _
which are given. for purposes of illustration and
are not to be considered‘as limiting my invention
,
I
“Germ
H
NI >
; 15 to ‘the particular details described therein.
2
V
substituted
in which X alky1
and Y
radicals
are hydrogen
such asalkoxyalkyl,
or alkyl and I'
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Example
1
49 ' Parts ' of z'sulphan?amldo'4'methoxypynm'
.
_
cyanoalkyl, aralkyl, dialkylaminoalkyl, etc.’
idine were mixed with 400 parts of methanol
It can readily be seen in the above formula that 20 and 200 parts of anhydrous ammonia and heated
when the 2-sulphanilamido-e-alkoxypyrimidine
for one hour at110° C. in an autoclave. After
is reacted with ammonia, then X and’ Y are hycooling and the release of pressure, the alcohol
drogen; when a primary amine such as methylWaS' evaporated The 2-S111Phani1amid0-4-ami
amine is used, then X15 met-11571 and Y is hydro- _ ' nopyrimidine was obtained by extraction of the
gen; and when a secondary amine, is used such '25 residue with dilute alkali and precipitation from
as dimethylamine, both X and Y are methyl. _ ‘
the alkaline solution by neutralization.
These compounds are useful as chemotherapeu- -
tic agents and, also, as intermediates in the preparation of other compounds.
The present invention 'is not particularly con-
A yield
of 23 parts was obtained melting with decomposi
tion at 259° to 270° C\,
T
'
30
Example 2 '
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.
cerned with the method by which the 2-sulphanilamido-é-alkoxypyrimidine is produced and it may
80 parts of 2-sulphanilamido-4-methoxypyrim
idine and 33 Parts Of vrdiethylaminopropyla
be produced by any suitable process. These com-
mine were heated together at 110° C‘. for 45 min
pounds have been prepared by reacting p-nitroutes; 'I'h'e semi-liquid reaction mixture gave off 7
benzene sulphonyl chloride with 2-amino-4-al- 35 ‘gas and set to a solid. The reaction product was
koxypyrimidines followed by reduction to produce
suspended in water and ?ltered. The solid 2
2-su1phanilamido-4-alkoxypyrimidines.
su1phani1amidO—4-(gamma — diethylaminopropyl
Illustrative examples of the amines which‘ may
amino) pyrimidine was crystallized from water
be used in carrying out the invention are as foland had a melting point of 230° to 232° C.
lows: methylamine, ethylamine, propylamine, 40 I claim:
butylamine, isopropylamine, amylamine, hexyl1- A method of preparing 2—Sulphani1amid0-4
amine, phenethylamine, cyanoethylamine, phenoxyethylamine, ethoxyeth'ylamine, diethylaminoisoamylamine, diethylaminopropylamine, di-
aminopyrimidines which comprises heating 170
gether a 2,- sulphanilamido—4-alkoxypyrimidine,
having the formula
methylaminopropylamine, dipropylaminopropyl- 45
amine, dipropylaminobutylamine, etc.
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When my invention is carried out using am-
N
NHEOSOKNEF<
monia or a volatile amine, it is preferable to use
>
a solvent such as methanol, ethanol, propanol,
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OR
>
N
V
butanol, etc., and to conduct the reaction in. a 50 in Which R is an alkyl radical, and a member of
closed vesse1 such as an autoclave,
the class consisting of ammonia, primary amines
In carrying outithe invention, the amine is
heated with a 2-sulphanilamido-4-alkoxypyrimie
and Secondary amines-
,
V
.
.
2- A method of preparing 2-S111Phani18/mid0-4—
dine such as 2-sulphanilamidor4-methoxypyrimiaminopyrimidines which comprises heating to-~
dine, 2-.-sulphanilamido-4-ethoxypyrimidine, etc.', 55 gether at a temperature between 50° and 200° C.,
2,403,713
3
4
2-su1phanilamido - 4 - methoxypyrimidine and a
member of the class consisting of ammonia, pri
mary amines and secondary amines.
3. A method of preparing 2-su1phani1amido
5. A method of preparing 2-su1phani1amido-4
aminopyrimidine which comprises heating to
gether 2-su1phani1amido - 4 - methoxypyrimidine
and ammonia.
6. A method of preparing 2-sulphani1amido-4
pyrimidines bearing in the 4-position a- secondary
amino group comprising heating together 2
su1phani1amido-4emethoxypyrimidine and a pri
comprises heating together 2-su1phani1amido-4
mary amine.
methoxypyrimicline and V-diethylaminopropyla
4. A method of preparing 2-sulphani1amido
pyrimidines bearing in the 4-position a, tertiary 10
amino group comprising heating together 2
su1ph-ani1amido-4~methoxypyrimidine and a sec
ondary amine.
-
.
(y-diethy1aminopropy1amino) pyrimidine which
mine.
i
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JACKSON P. ENGLISH.
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