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通过2,6 - 二氯嘌呤的铁或钯催化交叉偶联反应高效合成2 - 取代的6 - 甲基嘌呤碱基和核苷。

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

作者信息

Hocek Michal, Dvoráková Hana

机构信息

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, CZ-16610 Prague 6, Czech Republic.

出版信息

J Org Chem. 2003 Jul 11;68(14):5773-6. doi: 10.1021/jo034351i.

DOI:10.1021/jo034351i
PMID:12839482
Abstract

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-phenylpurines. 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.

摘要

9-取代或保护的2,6-二氯嘌呤与1当量的甲基氯化镁发生铁催化的交叉偶联反应，区域选择性地生成了产率良好的2-氯-6-甲基嘌呤。与3当量的甲基氯化镁进行相同反应或与三甲基铝进行钯催化反应可得到2,6-二甲基嘌呤。2-氯-6-甲基嘌呤与苯硼酸进行另一次偶联反应，生成6-甲基-2-苯基嘌呤。所有反应均针对苄基和四氢吡喃保护的嘌呤碱以及酰基保护的核糖苷和2-脱氧核糖苷进行。脱保护后，得到了游离的嘌呤碱和核苷。

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