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Efficient synthesis of 2-substituted thieno[2,3-d]pyrimidin-4(3H)-ones via an iminophosphorane

✍ Scribed by Zheng-Dong Fang; Yang-Gen Hu; Ming-Wu Ding

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
140 KB
Volume
19
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

The carbodiimides 4, obtained from reactions of iminophosphorane 3 with aromatic isocyanates, were reacted with secondary amines to give 2‐dialkylamino‐5‐ethyl‐6‐methyl‐thieno[2,3‐d]pyrimidin‐4(3__H__)‐ones 6 in the presence of catalytic amount of EtONa. Reactions of 4 with phenols or ROH in the presence of the catalytic amount of K2CO~3~ or RONa gave 2‐aryloxy‐ or 2‐alkoxy‐5‐ethyl‐6‐methyl‐thieno[2,3‐d]pyrimidin‐4(3__H__)‐ones 6 in satisfactory yields. The effects of the nucleophiles on cyclization have been investigated. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:266–270, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20424

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