Unusual Nucleophilic Addition of Grignard Reagents in the Synthesis of 4-Amino-pyrimidines.

Author(s) Tinson, R.A.J.; Hughes, D.L.; Ward, L.; Stephenson, R.
Journal ACS Omega
Date Published 2018 Aug 31

Pyrimidines have always received considerable attention because of their importance in synthesis and elucidation of biochemical roles, in particular that of vitamin B1. Herein, we describe a reaction pathway in a Grignard reagent-based synthesis of substituted pyrimidines. A general synthesis of α-keto-2-methyl-4-amino pyrimidines and their C6-substituted analogues from 4-amino-5-cyano-2-methylpyrimidine is reported. The presence of the nitrile substituent in the starting material also results in an unusual reaction pathway leading to C6-substituted 1,2-dihydropyrimidines. Grignard reagents that give normal pyrimidine products under standard reaction conditions can be switched to give dihydropyrimidines by holding the reaction at 0 °C before quenching.

DOI 10.1021/acsomega.8b01137
ISSN 2470-1343
Citation ACS Omega. 2018;3(8):89378944.

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