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Paper | Special issue | Vol 37, No. 1, 1994, pp.501-514
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S39
Synthesis of Pyrimidinyl Triflates and Palladium-catalyzed Coupling with Organotin and Organozic Reagents

Jessie Sandosham and Kjell Undheim*

*Department of Chemistry, University of Oslo, P.O.Box 1033, Blindern, N-0315 Oslo, Norway

Abstract

Pyrimidinyl triflates have been synthesized from pyrimidinones using triflic anhydride in the presence of triethylamine. The triflates, in the pyrimidine electrophilic positions, are versatile intermediates for substitution reactions. Carbon substituents are readily introduced in any position by Pd-catalyzed coupling reactions between pyrimidinyl triflates and aryl- or alkenyltin or with the corresponding organozinc reagents. Organozinc reagents are generally more reactive in coupling reaction and will effect the introduction of alkyl substituents.