One-Pot Acid-Promoted Synthesis of 6-Aminopyrazolopyrimidines from 1 H-Pyrazol-5-yl- N, N-dimethylformamidines or 5-Amino-1 H-pyrazole-4-carbaldehydes with Cyanamide

J Org Chem. 2019 Dec 20;84(24):16157-16170. doi: 10.1021/acs.joc.9b02653. Epub 2019 Nov 27.

Abstract

A convenient and efficient one-pot acid-promoted synthesis of 6-aminopyrazolo[3,4-d]pyrimidine has been developed by treatment of 1H-pyrazol-5-yl-N,N-dimethylformamidines or 5-amino-1H-pyrazole-4-carbaldehydes with cyanamide (NH2C≡N) in an acid-mediated solution. This synthetic route involves four steps of deprotection, imination, the key acid-promoted heterocyclization, and aromatization. On the basis of optimized studies, methanesulfonylchloride is considered to be the best solvent. Furthermore, the microwave-assisted synthetic technique was also carried out to improve the major product 6-aminopyrazolo[3,4-d]pyrimidines in this method. Moreover, our proposed mechanism was confirmed in this study, which demonstrates that N-[(5-amino-1,3-diaryl-1H-pyrazol-4-yl)methylene]cyanamide is the intermediate.

Publication types

  • Research Support, Non-U.S. Gov't