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SYNTHESIS OF NEW PYRIDO[2,3-d]PYRIMIDIN-5-ONE, PYRIDO[2,3-d]PYRIMIDIN-7-ONE, AND PYRIMIDINO[4,5-d][1,3]OXAZINE DERIVATIVES FROM 5-ACETYL-4-AMINOPYRIMIDINES

Alexander V. Komkov, Mikhail A. Kozlov, Andrey S. Dmitrenok, Nataliya G. Kolotyrkina, Mikhail E. Minyaev, Igor V. Zavarzin
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Abstract


Methods were developed for the synthesis of new pyrido[2,3-d]pyrimidine and pyrimidino[4,5-d][1,3]oxazine derivatives. When heated under reflux with MeONa in BuOH, 5-acetyl-4-aminopyrimidines, acylated with carboxylic anhydrides or acid chlorides, are transformed into pyrido[2,3-d]pyrimidin-5-one derivatives, i.e., the acetyl methyl group and the amide carbonyl moiety are involved in the cyclization. In the presence of an activated CH2 group (e.g., PhCH2) in the amide moiety, the cyclization involves this group and the acetyl carbonyl giving rise to pyrido[2,3-d]pyrimidin-7-one derivatives. The reaction of 5-acetyl-4-aminopyrimidines with carboxylic acid chlorides under reflux in xylene followed by addition of a base affords pyrimidino[4,5-d][1,3]oxazines.

Keywords


5-acetyl-4-aminopyrimidines; pyrido[2,3-d]pyrimidin-5-ones; pyrido[2,3-d]pyrimidin-7-ones; pyrimidino[4,5-d][1,3]oxazines; acylation; base-catalyzed cyclization

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