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Paper | Regular issue | Vol 85, No. 5, 2012, pp.1089-1103
Published online, 22nd March, 2012
DOI: 10.3987/COM-12-12432
Syntheses of 5-Amino-2-phenyl-4(3H)-pyrimidinone Derivatives Starting with Glycine

Daisuke Takahashi,* Yutaka Honda, and Kunisuke Izawa*

*Research Institute for Bioscience products and Finechemicals, Ajinomoto Co., Inc., 1780 Hinaga, Yokkaichi, Mie, 510-0885, Japan

Abstract

N-Cbz derivative of 5-amino-2-phenyl-4(3H)-pyrimidinone was prepared from sodium salt of methyl hydroxymethylene glycinate and benzamidine hydrochloride in good yield. However, the reaction with N-substituted benzamidine did not proceed to give the desired pyrimidinone. In contrast, the reaction of 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone readily prepared from hippuric acid and N-substituted benzamidine proceeded nicely to give 5-(benzoylamino)-6-oxo-2-phenyl-1(6H)-pyrimidineacetic acid in high yield.