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Synthesis 2008(13): 2127-2133  
DOI: 10.1055/s-2008-1067094
PAPER
© Georg Thieme Verlag Stuttgart · New York

Microwave-Assisted Silylation-Amination of Uracil Acyclonucleosides to 4-Alkylamino-2(1H)-Pyrimidinone Analogues

Vincent Roya, Adam Mieczkowskia, Dimitri Topalisb, Sabine Berteina-Raboinb, Dominique Deville-Bonneb, Steven P. Nolanc, Luigi A. Agrofoglio*a
a Institut de Chimie Organique et Analytique, UMR 6005, Université d’Orléans, 45067 Orléans, France
Fax: +33(2)38417281; e-Mail: luigi.agrofoglio@univ-orleans.fr;
b Laboratoire d’Enzymologie Moléculaire et Fonctionnelle, FRE CNRS 2852, Université Pierre & Marie Curie, 4 place Jussieu, 75005 Paris, France
c Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain
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Publication History

Received 10 March 2008
Publication Date:
16 May 2008 (online)

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Abstract

The synthesis of acyclic N4-substituted cytosine nucleoside phosphonates using a microwave-assisted N4-silylation-amination and olefin cross-metathesis as key assembly steps is described. The microwave-assisted silylation-amination is compared to a conventional heating protocol. While yields and purities of the coupling products were comparable under both conditions, microwave heating allows a significant acceleration of the reaction (from 48 h to 5 h).

Key words

microwaves - silylation-amination - olefin cross-metathesis­ - acyclic nucleoside phosphonates