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Note | Special issue | Vol 67, No. 2, 2006, pp.763-768
Published online, 14th October, 2005
DOI: 10.3987/COM-05-S(T)40
Palladium-catalyzed Arylation of Diisopropyl Malonate Applied to the Efficient Synthesis of the Selective MMP Inhibitor 5-(4-Phenoxyphenyl)-5-[4-(2-pyrimidinyl)-1-piperazinyl]barbituric Acid

Stanley Hutchings, Wen Liu, and Roumen Radinov*

*Chemical Synthesis Department, Hoffmann - La Roche Inc., Building 66, 340 Kingsland Street, Nutley, NJ 07110-1199, U.S.A.

Abstract

An efficient synthesis of the highly selective MMP inhibitor 5-(4-phenoxyphenyl)-5-[4-(2-pyrimidinyl)-1-piperazinyl]barbituric acid is reported. The title compound was prepared in three steps and 72% overall yield from 4-bromophenyl phenyl ether via an improved arylation of diisopropyl malonate.