Simple pyrimidines. XVI. A synthetic route to some 2-(Pyrimidin-2'-yl)acetic acids and esters

Abstract

A general route to the hitherto inaccessible 2-(pyrimidin-2?-yl)acetic acid (3a), its 4?-substituted derivatives, and their esters is described. For example, amidinoacetamide (1; R¹ = R² = NH₂) and ethyl benzoylacetate (2; R = Ph) give 2-(4?-hydroxy-6?-phenylpyrimidin-2?- yl)acetamide (3m) which with phosphoryl chloride gives 2-(4?-chloro-6?- phenylpyrimidin-2?-yl)acetonitrile (3n). The nitrile is converted into the corresponding imidic ester (3o) and thence into the carboxylic ester (3p) which undergoes dehalogenation to methyl 2-(4?- phenylpyrimidin-2?-yl)acetate (3q) and subsequent hydrolysis to 2-(4?- phenylpyrimidinyl)acetic acid (3r).