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Study on the regioselective alkylation of 2-thiopyrimidine

Yang Xu, Hua Yang, Jin Hu, Xiao-Wei Wang, Jun-Yi Liu*   

  1. Department of Chemical Biology, School of pharmaceutical Sciences, Peking University, Beijing 100083, China
  • Received:2007-01-10 Revised:2007-05-10 Online:2007-06-15 Published:2007-06-15
  • Contact: Jun-Yi Liu*

Abstract:

Aim To investigate the alkylation of 2-thiopyrimidine. Methods Treating the starting material 2-thiopyrimidine with chloromethyl ethers via a procedure of K2CO3 in DMF or with alkyl halide in CH3ONa-CH3OH at room temperature, to obtain the corresponding regioselective 2-S-allkyl pyrimidines. The products were determined by 1H NMR, 2D NMR, IR and MS spectra. Results 2-S-alkyl-pyrimidines were regioselectively synthesized. Conclusion In different conditions with different alkyl halides, 2- thiouracil could be converted into the corresponding 2-S-alkylpyrimidines regioselectively.

Key words: Alkylation, Alkylation, 2-Thio-6-methyl-uracil, 2-Thio-6-methyl-uracil, 2-Alkylthiopyrimidine, 2-Alkylthiopyrimidine, 6-Methyl-3,4-dihydro-2H-pyrido [2,1-b] [1,3] thiazin-8-one, 6-Methyl-3,4-dihydro-2H-pyrido [2,1-b] [1,3] thiazin-8-one

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