685894-52-4Relevant academic research and scientific papers
Synthesis of 5-mono- and 5,7-diamino-pyrido[2,3-d]-pyrimidinediones with potential biological activity by regioselective amination
Van Tinh, Dang,Stadibauer, Wolfgang
, p. 821 - 829 (2008/09/21)
(Chemical Equation Presented) 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 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-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.
