Synthesis of 5-mono- and 5,7-diamino-pyrido[2,3-d]-pyrimidinediones with potential biological activity by regioselective amination

✍ Scribed by Dang Van Tinh; Wolfgang Stadlbauer

• Book ID: 102341241
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2008
• Tongue: English
• Weight: 431 KB
• Volume: 45
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570450329

✦ Synopsis

Abstract

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5‐Alkyl‐/arylamino‐ and 5,7‐dialkyl/arylamino‐pyrido[2,3‐d]pyrimidine‐2,4‐diones (4,5, 7‐9) were prepared from the corresponding 5,7‐dichloro‐pyrido[2,3‐d]pyrimidine‐2,4‐diones 2 with aliphatic and aromatic amines 3 and 6 in a regioselective reaction. The 7‐monoazides 10, obtained by azidation of 5‐amino‐7‐chloro derivatives 4, were converted to iminophosphoranes by reaction with triphenyl‐phosphane via Staudinger reaction. Hydrolysis with aqueous acetic acid produced in one step 7‐unsubstituted‐amino‐pyrido[2,3‐d]pyrimidine‐2,4‐diones 12. In a similar amination reaction, 5‐chloropyrido[2,3‐d]pyrimidine‐2,4,7‐triones 13 were aminated and formylated to 5‐alkyl/arylamino‐6‐formyl derivatives 14‐16 in a combined one‐step‐reaction with bulky arylamines or alkylamines in the presence of dimethylformamide.