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Synthesis of pyrido[2,3-d]pyrimidines from aminopyrimidinecarbaldehydes

✍ Scribed by Francisco Perandones; José L. Soto

Publisher: Journal of Heterocyclic Chemistry
Year: 1998
Tongue: English
Weight: 568 KB
Volume: 35
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570350226

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✦ Synopsis

Abstract

2‐Methoxy‐4‐amino‐5‐pyrimidinecarbaldehyde (2a) as well as its 6‐methyl 2b and 6‐phenyl derivatives 2c were prepared by reduction of the corresponding aminopyrimidinecarbonitriles 1. Catalytic hydrogenation of 1a, 1b gives 5‐hydroxymethylpyrimidines 3a, 3b; under the same conditions 1c afforded 5‐aminomethylpyrimidine 4. Condensation of 2 with carbonitriles, ketones and polyfunctional carbonyl compounds bearing the ‐CH~2~CO‐ moiety afforded the pyrido[2,3‐d]pyrimidines and pyrimido‐[4,5‐b]quinoline derivatives.

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