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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (10): 1271-1273. 上一篇    下一篇

研究简报

HIV-1 RT抑制剂研究I. 1,3-二苄基-6-(3,4-环氧丁基)尿嘧啶的合成

王孝伟, 张志丽, 刘杰, 马小艳, 刘俊义*   

  1. 北京大学药学院化学生物学系 北京 100083
  • 收稿日期:2004-01-05 修回日期:2004-03-30 接受日期:2004-04-19 发布日期:2022-09-20
  • 基金资助:
    国家自然科学基金(No. 20172007)资助项目.

Study on HIV-1 RT Inhibitor I. Synthesis of 1,3-Dibenzyl-6-(3,4-epoxybutyl)uracil

WANG Xiao-Wei, ZHANG Zhi-Li, LIU Jie, MA Xiao-Yan, LIU Jun-Yi*   

  1. Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100083
  • Received:2004-01-05 Revised:2004-03-30 Accepted:2004-04-19 Published:2022-09-20
  • Contact: * E-mail: jyliu@bjmu.edu.cn

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报道了1,3-二苄基-6-(3,4-环氧丁基)尿嘧啶的合成新方法.以6-甲基尿嘧啶(1)为起始物,经1,3-二苄基-6-甲基尿嘧啶(2)及未见文献报道的1,3-二苄基-6-(3-丁烯基)尿嘧啶(3)和1,3-二苄基-6-(3-羟基-4-溴丁基)尿嘧啶(4),首次高收率合成了1,3-二苄基-6-(3,4-环氧丁基)尿嘧啶(5),并对其化学结构进行了表征.

关键词: 1,3-二苄基-6-(3-丁烯基)尿嘧啶, 1,3-二苄基-6-(3-羟基-4-溴丁基)尿嘧啶, 1,3-二苄基-6-(3,4-环氧丁基)尿嘧啶.

An efficient practical synthetic method for preparing 1,3-dibenzyl-6-(3,4-epoxybutyl) uracil (5) has been realized from 6-methyluracil (1). The title compound 5 is a key intermediate compound of HIV-1RT and methionine synthase inhibitors. 6-Methyluracil (1) was used as starting material to react with benzyl bromide giving 1,3-dibenzyl-6-methyluracil (2), which reacted with allyl bromide to afford 1,3-dibenzyl-6-(3-butenyl)uracil (3). Compound 3 reacted with NBS in DMSO-H2O to yield4, which was converted into the title compound 5 under basic conditions in good yield.

Key words: 1,3-dibenzyl-6-(3-butenyl)uracil, 1,3-dibenzyl-6-(3-hydroxyl-4-bromobutyl)uracil, 1,3-dibenzyl-6-(3,4-epoxybutyl)uracil