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Abstract <p>To date, the reported synthetic methods for 2-hydrazino-4,6-dimethylpyrimidine have not been sufficiently convenient and have yielded less than optimal results. In this study, we report an optimized three-step synthesis of 2-hydrazino-4,6-dimethylpyrimidine starting from 4,6-dimethylpyrimidine-2-thiol with the yield of 88.4%. The advantages of this procedure include the elimination of precious metal catalysts, simplified operation, short reaction time, and significantly enhanced yields. Meanwhile, we speculate that the plausible mechanism underlying the formation of 2-hydrazino-4,6-dimethylpyrimidine involves the lone pair of electrons on the nitrogen atom of hydrazine hydrate initially attacking the C=N double bond in the pyrimidine ring through a 1,2-nucleophilic addition, forming an unstable transition-state intermediate. This intermediate subsequently undergoes proton transfer and cleavage of the α-bond, resulting in the elimination of the ethyl 2-hydrosulfonylacetate moiety and the formation of 2-hydrazino-4,6-dimethylpyrimidine.</p>

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An Efficient Novel Method for Synthesis of 2-Hydrazino-4,6-dimethylpyrimidine

  • 期刊论文

  • 发表日期：

    2025年11月1日

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  • Pei Li,
  • Qing Liu,
  • Xiao-Shuang Ran,
  • Fan-Miao Zhang,
  • Dan Wang,
  • Wen-Ting Mei,
  • Xiang Wang

摘要

Abstract

To date, the reported synthetic methods for 2-hydrazino-4,6-dimethylpyrimidine have not been sufficiently convenient and have yielded less than optimal results. In this study, we report an optimized three-step synthesis of 2-hydrazino-4,6-dimethylpyrimidine starting from 4,6-dimethylpyrimidine-2-thiol with the yield of 88.4%. The advantages of this procedure include the elimination of precious metal catalysts, simplified operation, short reaction time, and significantly enhanced yields. Meanwhile, we speculate that the plausible mechanism underlying the formation of 2-hydrazino-4,6-dimethylpyrimidine involves the lone pair of electrons on the nitrogen atom of hydrazine hydrate initially attacking the C=N double bond in the pyrimidine ring through a 1,2-nucleophilic addition, forming an unstable transition-state intermediate. This intermediate subsequently undergoes proton transfer and cleavage of the α-bond, resulting in the elimination of the ethyl 2-hydrosulfonylacetate moiety and the formation of 2-hydrazino-4,6-dimethylpyrimidine.