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Synthesis 2015; 47(14): 2100-2124
DOI: 10.1055/s-0034-1380200
DOI: 10.1055/s-0034-1380200
paper
Regioselective Synthesis of 2-Aryl-4-(arylethynyl)- and 2,4-Bis(arylethynyl)pyrrolo[2,3-d]pyrimidines
Further Information
Publication History
Received: 26 February 2015
Accepted after revision: 20 March 2015
Publication Date:
29 April 2015 (online)
Abstract
A comparative study of Sonogashira and Stille reactions, as well as Suzuki and Stille reactions, for the introduction of alkynyl and aryl moieties onto the pyrrolo[2,3-d]pyrimidine framework is carried out. General and regioselective methods for the preparation of 4-(arylethynyl)-2-chloro-, 2,4-bis(arylethynyl)pyrrolo[2,3-d]pyrimidines and 2-aryl-4-(arylethynyl)pyrrolo[2,3-d]pyrimidines by coupling of 2,4-dichloro-7-methylpyrrolo[2,3-d]pyrimidine with the corresponding (arylethynyl)tributyl- or (aryl)tributylstannanes are developed. The established protocols tolerate many substituents and enable the preparation of pyrrolopyrimidines with electronically diverse π-conjugated assemblies and different linking topologies on the pyrrolo[2,3-d]pyrimidine scaffold.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380200.
- Supporting Information
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