Direct B-Alkyl Suzuki-Miyaura Cross-Coupling of 2-Halopurines. Practical Synthesis of ST1535, a Potent Adenosine A2A Receptor Antagonist

被引：14
|
作者：
Bartoccini, Francesca [1 ]
Cabri, Walter [2 ]
Celona, Diana [2 ]
Minetti, Patrizia [2 ]
Piersanti, Giovanni [1 ]
Tarzia, Giorgio [1 ]
机构：
[1] Univ Urbino Carlo Bo, Dept Drug & Hlth Sci, Pzza Rinascimento 6, I-61029 Urbino, PU, Italy
[2] Sigma Tau Pharmaceut Co, Chem & Analyt Dev Dept, I-00040 Rome, Italy
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 15期
关键词：
KINASE INHIBITORS; 2,6,9-TRISUBSTITUTED PURINES; ARYL CHLORIDES; NUCLEOSIDES; DERIVATIVES; EFFICIENT; VERSATILE; CATALYST; BROMIDES; RATS;
D O I：
10.1021/jo101027h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The scope and limitations of using palladium-catalyzed cross-coupling reactions of diverse butyl metal species with two different 2-halopurines were evaluated. While tributylboranes reacted readily and regioselectively with both 2-chloro-6-dibenzylaminopurines and 2-iodo-6-chloropurines, all the other alkyl metal species were much less reactive and gave very poor yield and/or selectivity of the desired product. This protocol was applied to the synthesis of an important adenosine A(2A) receptor antagonist, ST1535.
引用
收藏
页码：5398 / 5401
页数：4
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