Synthesis of 6-Amino-, 6-Methyl- and 6-Aryl-2-(hydroxymethyl)purine Bases and Nucleosides

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Title:Synthesis of 6-Amino-, 6-Methyl- and 6-Aryl-2-(hydroxymethyl)purine Bases and Nucleosides
Creators:
Šilhár, Peter
Pohl, Radek
Votruba, Ivan
Klepetářová, Blanka
Hocek, Michal
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 71, 6, pp. 788-803
Uncontrolled Keywords:X-Ray diffraction, Hydroxymethylation, Palladium, Purines, Nucleosides, Cytostatic activity, Functionalized organozinc reagents, Cross-coupling reactions

Abstract

An efficient methodology of the synthesis of 6-substituted 2-(hydroxymethyl)purine derivatives (bases and nucleosides) was developed. Regioselective Pd-catalyzed cross-coupling reactions of 6-chloro-2-iodopurines with [(benzoyloxy)methyl]zinc iodide gave 2-[(benzoyloxy)-methyl]-6-chloropurines that were converted to 2-(hydroxymethyl)adenines by reactions with ammonia and to 6-methyl- or 6-aryl-2-(hydroxymethyl)purines by cross-coupling reactions with trimethylaluminium or arylboronic acids followed by deprotection. The title 6-substituted 2-(hydroxymethyl)purine bases and nucleosides did not exhibit significant cytostatic or anti-HCV activity. <p>

Title:Synthesis of 6-Amino-, 6-Methyl- and 6-Aryl-2-(hydroxymethyl)purine Bases and Nucleosides
Creators:
Šilhár, Peter
Pohl, Radek
Votruba, Ivan
Klepetářová, Blanka
Hocek, Michal
Uncontrolled Keywords:X-Ray diffraction, Hydroxymethylation, Palladium, Purines, Nucleosides, Cytostatic activity, Functionalized organozinc reagents, Cross-coupling reactions
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:71
Number:6
Page Range:pp. 788-803
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20060788UNSPECIFIED
ID Code:2507
Item Type:Article
Deposited On:06 Feb 2009 17:19
Last Modified:06 Feb 2009 16:19

Citation

Šilhár, Peter; Pohl, Radek; Votruba, Ivan; Klepetářová, Blanka; Hocek, Michal (2006) Synthesis of 6-Amino-, 6-Methyl- and 6-Aryl-2-(hydroxymethyl)purine Bases and Nucleosides. Collection of Czechoslovak Chemical Communications, 71 (6). pp. 788-803. ISSN 0010-0765

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