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Synthesis 2002(4): 0538-0542
DOI: 10.1055/s-2002-20970
PAPER
© Georg Thieme Verlag Stuttgart · New York

Dimethylpyridin-4-ylamine-Catalysed Alcoholysis of 2-Amino-N,N,N-trimethyl-9H-purine-6-ylammonium Chloride: An Effective Route to O6-Substituted Guanine Derivatives from Alcohols with Poor Nucleophilicity

Ralf Schirrmacher, Björn Wängler, Esther Schirrmacher, Thorsten August, Frank Rösch
Department of Nuclear Chemistry, Section Radiopharmaceutical Chemistry, University of Mainz, Fritz-Strassmann-Weg 2, 55128 Mainz, Germany
Fax: +49(6131)3924510; e-Mail: schirrmacher@mail.kernchemie.uni-mainz.de;
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Publication History

Received 20 November 2001
Publication Date:
28 July 2004 (online)

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Abstract

Dimethylpyridin-4-ylamine (DMAP)-catalysed reactions of 2-amino-N,N,N-trimethyl-9H-purine-6-ylammonium chloride with fluoropyridine methoxides and various other alkoxides in DMSO at 60 °C gave the corresponding coupling products in moderate to good yields between 20-87%. Under these reaction conditions, fluorinated O6-substituted Guanine derivatives have been synthesized which could not be obtained via known analogous literature procedures. The respective yields of known O6-substituted guanine derivatives could be significantly improved by using this method. The efficient use of DMAP as an excellent nucleophilic catalyst in the syntheses of O6-substituted Guanine derivatives has thus been demonstrated.

Key words

catalysis - coupling - fluorine - nucleophilic aromatic substitution - pyridines

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