Catalytic alkynone generation by Sonogashira reaction and its application in three-component pyrimidine synthesis

• DOI: 10.1038/nprot.2008.152
• Publication Date: 2008-10-02T10:03:21Z
• Authors: Daniel M D'Souza; Thomas J J Müller
• Keywords: Pyrimidines; Chlorides; Molecular Structure; Ethylamines; 01 natural sciences; Catalysis; Copper; Palladium; 0104 chemical sciences

The Sonogashira alkynylation of acid chlorides can be efficiently conducted in less than an hour by performing the reaction in tetrahydrofuran as a solvent and in the presence of one stoichiometrically necessary equivalent of triethylamine as a base. This approach also opens new avenues for consecutive one-pot multicomponent reactions. As an example, the one-pot three-component pyrimidine synthesis illustrates the versatility of this modified Sonogashira protocol as an entry to diversity-oriented heterocycle synthesis in a one-pot fashion. The protocol can be completed within a few hours.