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2005
Pyrazine derivatives
R 0550
Solution-Phase Parallel Synthesis of an N-Alkylated Dihydropteridinone Library
Fluorous Amino Acids. — The route to title compounds of type (VII) starts with
12- 167 from
two displacement reactions of pyrimidine (II), first with 4 different fluorous amino
acids (I), and then with 5 different secondary amines. The hydrogenation of the nitro
group followed by microwave-assisted cyclization affords the dihydropteridinones.
Further diversification is introduced by regioselective N-alkylation of compounds (V)
with 5 different benzyl halides. The reaction intermediates and final products are purified by fluorous solid-phase extraction or precipitation without the need to perform
chromatography. — (NAGASHIMA, T.; ZHANG*, W.; J. Comb. Chem. 6 (2004) 6,
942-949; Univ. Pittsburgh Appl. Res. Cent., Fluorous Technol., Inc., Pittsburgh,
PA 15238, USA; Eng.) — Klein
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