An efficient synthesis of 2-substituted 6-methylpurine bases and nucleosides by Fe- or Pd-catalyzed cross-coupling reactions of 2,6-dichloropurines

被引：84

作者：

Hocek, M ^{[1
]}

Dvoráková, H

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CZ-16610 Prague 6, Czech Republic

[2] Prague Inst Chem Technol, Cent NMR Lab, CZ-16628 Prague, Czech Republic

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 14期

关键词：

D O I：

10.1021/jo034351i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fe-catalyzed cross-coupling reactions of 9-substituted or protected 2,6-dichloropurines with 1 equiv of methylmagnesium chloride gave regioselectively 2-chloro-6-methylpurines in good yields. The same reactions with 3 equiv of methylmagnesium chloride or Pd-catalyzed reactions with trimethylaluminum afforded 2,6-dimethylpurines. The 2-chloro-6-methylpurines underwent another coupling with phenylboronic acid to give 6-methyl-2-phenyipurines. All reactions were perfomed for Bn- and THP-protected purine bases as well as for acyl-protected ribosides and 2-deoxyribosides. After deprotection, free purine bases and nucleosides were obtained.

引用

页码：5773 / 5776

页数：4

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