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

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

• References

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