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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (2): 301-303. 上一篇    下一篇

研究简报

1,3-二(乙氧基甲基)-5-N,N-二甲氨基-6-甲基尿嘧啶的合成

马小艳a，王瑞平c，李阿敏a，陈艳丽a
王孝伟a，张志丽a，刘俊义*,a,b   

  1. (a北京大学药学院化学生物学系 北京100083)
    (b北京大学天然药物及仿生药物国家重点实验室 北京100083)
    (c首都医科大学化学生物学与药学学院 北京100069)
  • 收稿日期:2007-04-12 修回日期:2007-06-16 发布日期:2008-02-01
  • 通讯作者: 刘俊义

Synthesis of 1,3-(Diethoxymethyl)-5-N,N-dimethylamino-6-methyluracil

MA Xiao-Yana,WANG Rui-Pingc,LI A-Mina,CHEN Yan-Lia
WANG Xiao-Weia,ZHANG Zhi-Lia,LIU Jun-Yi*,a,b   

  1. (a Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100083)
    (b State Key Laboratory of Natural and Biomimetic Drug, Peking University, Beijing 100083)
    (c School of Chemical Biology and Pharmaceutical Sciences, Capital University, Beijing 100069)
  • Received:2007-04-12 Revised:2007-06-16 Published:2008-02-01
  • Contact: LIU Jun-Yi

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报道了1,3-二(乙氧基甲基)-5-N,N-二甲氨基-6-甲基尿嘧啶方便、高产率的合成方法. 以6-甲基尿嘧啶(1)为起始物, 经硝化、嘧啶N1,N 3-烷基化、还原及氨基甲基化, 首次高产率合成了1,3-二(乙氧基甲基)-5- N,N -二甲氨基-6-甲基尿嘧啶(5), 并对其化学结构进行了表征.

关键词: 1,3-二(乙氧基甲基)-5-N,N-二甲氨基-6-甲基尿嘧啶, 1,3-二(乙氧基甲基)-5-氨基-6-甲基尿嘧啶, 5-硝基-6-甲基尿嘧啶

A new practical approach to prepare 1,3-(diethoxymethyl)-5-N,N-dimethylamino-6-methyluracil (5) has been realized from 6-methyluracil (1). Compound 5 is a key intermediate material in the synthesis of HIV-1 RT and methionine synthase inhibitors. 6-Methyluracil (1) reacted with HNO3-P2O5 giving 5-nitro-6-methyluracil (2), which alky-lated at N1,N3 through reaction with ethoxymethyl chloride to give 3. Compound 3 was then reduced through treatment with HCOONH4-Pd/C and the derived C-5 amino group reacted with CH3I to convert into compound 5 in good yield.

Key words: 1,3-(diethoxymethyl)-5-amino-6- methyluracil, 1,3-(diethoxymethyl)-5-N,N-dimethylamino-6-methyluracil, 5-nitro-6-methyluracil