DFT Study on Two Plausible Mechanistic Routes to Pyrazolo[3,4-d]pyrimidine-4- Amines from Pyrazoloformimidate

Amal       Al-Azmi

doi:10.2174/1385272824666200203122450

Abstract

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.

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DOI https://dx.doi.org/10.2174/1385272824666200203122450	Print ISSN 1385-2728
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