136010-90-7

Upstream product

• 50427-77-5 5-amino-1-phenyl-1H-pyrazole-4-carboxamide 
• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 
• 136010-89-4 5-(3-benzoylthioureido)-1-phenylpyrazole-4-carboxamide 
• 4461-33-0 benzoyl isocyanate 

Downstream Products

• 136010-91-8 4-amino-1-phenylpyrazolo-<3,4-d>pyrimidin-6(5H)-one 
• 136010-91-8 4-Amino-1-phenyl-1H-pyrazolo [3,4-d] pyrimidin-6(7H)-one 
• 334972-33-7 6-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 

Relevant academic research and scientific papers

High-pressure synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines

The synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines has been performed by aromatic nucleophilic substitution of 4-amino-6-chloro-1-phenylpyrazolo[3,4-d]pyrimidine under conditions of high pressure at ambient temperature. Conventional synthetic conditions (reflux at atmospheric pressure) were unsuccessful. The S enantiomer 11 displayed higher affinity and selectivity for the adenosine A1 receptor than the R enantiomer 12.

Pyrazolo[3,4-d]pyrimidine analogues of isoguanine

4-Amino-1-phenyl-5H-pyrazolo[3,4-d]pyrimidin-6-one (5a) was synthesized in 68% yield in a one pot reaction involving the condensation of 5-amino-1-phenylpyrazole-4-carbonitrile with benzoyl isocyanate followed by an annulation with ammonia.

4-Amino-1-phenylpyrazolo-pyrimidin-6(5H)-one, an Isoguanosine Analogue

5-Amino-1-phenylpyrazole-4-carboxamide was condensed with benzoyl isothiocyanate.The resulting thiourea was treated with dicyclohexylcarbodiimide and annulated with ethanolic ammonia to yield 4-amino-1-phenylpyrazolopyrimidin-6(5H)-one.This product is a 1-phenylpyrazolopyrimidine analogue of the biologically active natural product, isoguanosine.