Synthesis 2007(24): 3815-3820  
DOI: 10.1055/s-2007-990882
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 4-Alkynylpyrrolo[2,3-d]pyrimidines by Palladium-Catalyzed Cross-Coupling Reactions

Sigitas Tumkevicius*, Viktoras Masevicius
Department of Organic Chemistry, Faculty of Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, Lithuania
Fax: +370(5)2330987; e-Mail: sigitas.tumkevicius@chf.vu.lt ;
Further Information

Publication History

Received 19 July 2007
Publication Date:
13 November 2007 (online)

Abstract

The palladium-catalyzed cross-coupling reaction of methyl­ 5-amino-4-chloro- and 5-amino-4-iodo-7-methyl-2-(methylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate with various terminal alkynes has been investigated. The 4-iodo derivative was found to be a good substrate for the synthesis of various 4-alkynylpyrrolopyrimidines. A simple synthesis of 4-(indol-2-yl)pyrrolo[2,3-d]pyrimidines by the reaction of 4-iodopyrrolopyrimidine with 2-ethynyl-N-mesylaniline in the presence dichlorobis(triphenylphosphine)palladium and copper(I) iodide is described.