Regioselective Synthesis of 2-Aryl-4-(arylethynyl)- and 2,4-Bis(arylethynyl)pyrrolo[2,3-d]pyrimidines

Jonas Bucevicius; Sigitas Tumkevicius

doi:10.1055/s-0034-1380200

Synthesis, Table of Contents

Synthesis 2015; 47(14): 2100-2124
DOI: 10.1055/s-0034-1380200

paper

Regioselective Synthesis of 2-Aryl-4-(arylethynyl)- and 2,4-Bis(arylethynyl)pyrrolo[2,3-d]pyrimidines

Authors

Jonas Bucevicius

Vilnius University, Faculty of Chemistry, Department of Organic Chemistry, Naugarduko 24, LT-03225 Vilnius, Lithuania Email: Sigitas.Tumkevicius@chf.vu.lt
Sigitas Tumkevicius*

Vilnius University, Faculty of Chemistry, Department of Organic Chemistry, Naugarduko 24, LT-03225 Vilnius, Lithuania Email: Sigitas.Tumkevicius@chf.vu.lt

Abstract

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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.

Key words

Stille reaction - alkynes - arylation - catalysis - heterocycles

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References

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Supplementary Material

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