Synthesis and Transformation of Methyl 2‐(6‐Hydroxy‐2‐phenylpyrimidin‐4‐yl)acetate: Simple Preparation of Pyrimidines with Heterocyclic Substituents

Abstract

A simple and efficient synthesis of four new substituted pyrimidines, compounds 9a -d, from the title compound 3 is described. Conversion of 3 to methyl (E)-3-(dimethylamino)-2-(6-methoxy-2-phenylpyrimidin-4-yl)prop-2-enoate (4), followed by condensation with various dinucleophiles according to the enaminone methodology, afforded the target compounds 9 in medium-to-good yields.

Transformation of 1,5-Diphenylpentane-1,3,5-trione. The Synthesis of Substituted (4H)-Pyranones, Pyridin-4(1H)-ones and 4H-Pyrano[3,2-c]pyridin-4-ones

“…23,24 As part of our interest, we have recently reported an efficient method for the preparation and functionalization of highly substituted 1-aminopyrroline, 1-aminopyrrole, and oxazoline-pyrroline fused system from 1,2-diaza-1,3-butadines and 3-dimethylaminopropenoates. 25 Recently, dialkyl acetonedicarboxylates as compounds with two activated methylene groups have been used as starting compounds for preparation of mono and bis(dimethylamino)methylidene intermediates which have been further transformed into 1-substituted 4-oxo-1,4-dihydropyridine-3,5-dicarboxylates, 26 2H-pyrazolo[4,3-c]pyridine-7-carboxylates, 27 hetero-aryl substituted pyrazoles, 28 heteroaryl substituted pyrimidines, 29 and pyrazolo [4,3-d] [1,2]diazepine-8carboxylates. 30,31 In this paper, we report transformations of 1,5-diphenylpentane-1,3,5-trione into substituted 5-benzoylpyran-4-one, 5-benzoylpyridin-4(1H)-one, 4H-pyrano[3,2-c]pyridin-4-one, and 1-substituted 3,5-dibenzoylpyridin-4(1H)-ones.…”