Mechanochemical Magnesium-Mediated Minisci C–H Alkylation of Pyrimidines with Alkyl Bromides and Chlorides

A novel method to synthesize 4-alkylpyrimidines by the mechanochemical magnesium-mediated Minisci reaction of pyrimidine derivatives and alkyl halides has been reported. The reaction process operates with a broad substrate scope and excellent regioselectivity under mild conditions with no requiremen...

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Bibliographic Details
Published in:Organic letters 2021-08, Vol.23 (16), p.6423-6428
Main Authors: Wu, Chongyang, Ying, Tao, Yang, Xinjie, Su, Weike, Dushkin, Alexandr V, Yu, Jingbo
Format: Article
Language:English
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Summary:A novel method to synthesize 4-alkylpyrimidines by the mechanochemical magnesium-mediated Minisci reaction of pyrimidine derivatives and alkyl halides has been reported. The reaction process operates with a broad substrate scope and excellent regioselectivity under mild conditions with no requirement of transition-metal catalysts, solvents, and inert gas protection. The practicality of this protocol has been demonstrated by the up-scale synthesis, mechanochemical product derivatization, and antimalarial drug pyrimethamine preparation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02241