Pyrazolo[3,4-d]pyrimidine-4-amine was prepared at room temperature in a catalyst-
free medium with moderate yield and characterized by spectroscopic and X-ray diffraction
techniques. Two possible mechanistic routes were suggested for its formation.
Route 1 entails attack by the N of the amine on the imidate carbon followed by Dimroth
rearrangement after cyclization. Route 2 is the nucleophilic attack by the amine on the CN
function followed by cyclization to pyrazolo[3,4-d]pyrimidine-4-amine. Density functional
theory (DFT) calculation studies of the two proposed reaction pathways illustrated that the
Route 2 reaction was more likely than that of Route 1.
Keywords: Pyrazole, DFT, pyrimidine, imidate, N-heterocycles, pyrazolopyrimidine.
Rights & PermissionsPrintExport