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

[ Vol. 24 , Issue. 2 ]

Author(s):

Amal Al-Azmi*   Pages 216 - 229 ( 14 )

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.

Affiliation:

Chemistry Department, Kuwait University, P. O. Box 5969, Safat 13060

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