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Syntheses of various 5‐(3′‐substituted phenyl)uracils

 

作者: Ulf Wellmar,   Anna‐Britta Hömfeldt,   Salo Gronowitz,  

 

期刊: Journal of Heterocyclic Chemistry  (WILEY Available online 1996)
卷期: Volume 33, issue 2  

页码: 409-414

 

ISSN:0022-152X

 

年代: 1996

 

DOI:10.1002/jhet.5570330232

 

出版商: Wiley‐Blackwell

 

数据来源: WILEY

 

摘要:

AbstractThe Suzuki Pd(0)‐catalysed coupling between arylboronic acids and aryl bromides or iodides in weakly alkaline medium has been used for the preparation of 5‐(3′‐chlorophenyl)‐, 5‐(3′‐iodophenyl)‐, 5‐(3′‐aminophenyl)‐, 5‐(3′‐azidophenyl)‐, 5‐(3′‐methylthiophenyl)‐ and 5‐(3′‐styryl)‐substituted 2,4‐di‐t‐butoxypyrimidines. In the coupling between 2,4 di‐t‐butoxy‐5‐pyrimidineboronic acid and the six different aryl halides that were used as coupling partners, only 1‐azido‐3‐bromobenzene did not give satisfactory yields, 18%. The other five aryl halides gave the desired 5‐(3′‐substituted phenyl)‐2,4‐di‐r‐butoxypyrimidines in 41–92% yield. Dealkylation of these five 5‐(3′‐substituted phenyl)‐2,4‐di‐t‐butoxypyrimidines in 2.5Mhydrochloric acid gave the corresponding 5‐(bromoaryl)uracils in almost quantitative yields. 5‐(3

 

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