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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (06): 918-922. 上一篇    下一篇

研究简报

4-氯-7H-吡咯并[2,3-d]嘧啶与2,4-二氯-7H-吡咯并[2,3-d]嘧啶的合成研究

郝宝玉1,2，陈新志*,1，张维汉2   

  1. 1浙江大学化工系 杭州 310027)
    (2和记黄埔医药有限公司 上海 201203
  • 收稿日期:2009-09-18 修回日期:2009-11-12 发布日期:2010-01-29
  • 通讯作者: 郝宝玉 E-mail:chiyuwang@163.com

Synthesis of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine and 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Hao Baoyu1,2 Chen Xinzhi*,1 Zhang Weihan2   

  1. 1 College of Chemical Engineering, Zhejiang University, Hangzhou 310027)
    (2 Hutchison Medipharma Limited, Shanghai 201203
  • Received:2009-09-18 Revised:2009-11-12 Published:2010-01-29
  • Contact: 郝宝玉 Hao Bao-Yu E-mail:chiyuwang@163.com

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报道了以廉价易得的丙二酸二乙酯为起始原料, 经过α-烷基化、环合、氯化、烯键氧化和SNAr/环化五步反应, 高收率地得到目标产物4-氯-7H-吡咯并[2,3-d]嘧啶(6)和2,4-二氯-7H-吡咯并[2,3-d]嘧啶(10)(总收率分别达到45.8%和44.8%)的合成方法, 并对中间体和产物的化学结构进行了表征.

关键词: 丙二酸二乙酯, α-烷基化, K2OsO4, SNAr/环化

An efficient route to synthesize 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (6) and 2,4-dichloro-7H- pyrrolo[2,3-d]pyrimidine (10) starting from diethyl malonate in five steps with the total yields of 45.8% and 44.8% was disclosed in the presented paper. The chemical structures of the objective products as well as the related intermediates were confirmed.

Key words: diethyl malonate, α-alkylation, K2OsO4, SNAr/cyclization