Mechanochemical Magnesium-Mediated Minisci C–H Alkylation of Pyrimidines with Alkyl Bromides and Chlorides
Chongyang Wu, Ying Tao, Xinjie Yang, Weike Su, Alexander V. Dushkin, Jingbo Yu
Abstract
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.
Topics & Concepts
ChemistryAlkylRegioselectivityMagnesiumAlkylationCatalysisHalidePyrimidineCombinatorial chemistryOrganic chemistryStereochemistryCatalytic C–H Functionalization MethodsPhenothiazines and Benzothiazines Synthesis and ActivitiesSynthesis and Reactivity of Heterocycles