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110. Synthesis of 5-Mono- and 5,7-Diamino-pyrido[2,3-d]pyrimidinediones with Potential Biological Activity by Regioselective Amination
Dang V. T. and W. Stadlbauer, in press (10/07)

Abstract:
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 11, obtained by azidation of 5-amino-7-chloro derivatives, were converted to iminophosphoranes by reaction with triphenylphosphane 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-chloro-pyrido[2,3-d]pyrimidine-2,4,8-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


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abstract scheme