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

页码：5398 / 5401

页数：4

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