Synthesis of 4-hydrazinopyrazolo[3,4-d]pyrimidines and their reactions with carbonyl compounds

Abstract

Synthesis of a new 4-hydrazinopyrazolo[3,4-d]pyrimidine was achieved via heating (4,6-dithioxo-1H-pyrazolo[3,4-d] pyrimidin-3-yl)acetonitrile with hydrazine hydrate. Reactions of the latter product with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues afforded the corresponding hydrazone and pyrazole derivatives, respectively. Similarly, condensation of 2-[6-(benzylsulfanyl)-4-hydrazino-1H-pyrazolo[3,4-d]pyrimidin-3-yl]acetonitrile with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues gave the respective hydrazone and pyrazolone derivatives. Alkylation reactions of 2-[4,6-bis(benzylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]acetonitrile with arylamines gave the respective 4-(N-arylamino)-6-benzylsulfanylpyrazolo[3,4-d] pyrimidine derivatives.