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Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (03): 295-298. Previous Articles     Next Articles

Original Articles

2-氨基噻吩并[2,3-d]嘧啶-4(3H)-酮衍生物的合成

胡扬根1, b，吕茂云1，宋鹤丽1，丁明武*,1   

  1. (1 华中师范大学化学学院 教育部农药与化学生物学重点实验室 武汉 430079)
    (2 郧阳医学院医用化学教研室 十堰 442000)
  • 收稿日期:2004-05-19 修回日期:2004-09-13 发布日期:2005-02-28
  • 通讯作者: 丁明武

Synthesis of 2-Amino-thieno[2,3-d]pyrimidin-4(3H)-ones

HU Yang-Gen1,2,LU Mao-Yun1,SONG He-Li1,DING Ming-Wu*,1   

  1. (1 Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry,
    Central China Normal University, Wuhan 430079)
    (2 Department of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000)
  • Received:2004-05-19 Revised:2004-09-13 Published:2005-02-28
  • Contact: DING Ming-Wu

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Ethyl 2-amino-4-ethylthiophene-3-carboxylate (2), obtained from reaction of butyraldehyde (1), ethyl cyanoacetate, sulfur and triethylamine, reacted with triphenylphosphine, hexachloroethane and triethylamine to give iminophosphorane 3 in 84% yield. Further aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates gave the carbodiimides 4, which were reacted with secondary amines to give 2-dialkylamino-thieno[2,3-d]pyrimidin-4(3H)-ones 6 in the presence of catalytic amounts of EtO－Na＋in 58%～82% yields.

Key words: thieno[2,3-d]pyrimidin-4(3H)-one, carbodiimide, synthesis, aza-Wittig reaction