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SYNTHESIS OF NOVEL PYRIMIDO[4,5-d]PYRIMIDINE DERIVATIVES FROM 5-ACETYL-4-AMINOPYRIMIDINES

Александр В. Комков, Михаил А. Козлов, Михаил A. Презент, Андрей С. Дмитренок, Наталья Г. Колотыркина, Михаил Е. Миняев, Игорь В. Заварзин
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Abstract


Two routes were proposed for the synthesis of pyrimido[4,5-d]pyrimidine derivatives from 5-acetyl-4-aminopyrimidines. Acylation of 5-acetyl-4-aminopyrimidines followed by cyclization by the action of NH4OAc made it possible to access pyrimido[4,5-d]pyrimidines with alkyl, aryl, and hetaryl substituents in positions 2 and 7. Reductive amination of the acetyl group in 5-acetyl-4-aminopyrimidines and subsequent cyclization with DMF–DMA or HC(OEt)3 resulted in the formation of 6-alkyl-3,4-dihydropyrimido[4,5-d]pyrimidines.

Keywords


5-acetyl-4-aminopyrimidines; 3,4-dihydropyrimido[4,5-d]pyrimidines; pyrimido[4,5-d]pyrimidines; heterocyclization; reductive amination.

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