Tetrahedron letters

Synthesis of 2-(2, 6-dichloro-4-pyridyl)-3-propargyl-5-ethyl-6-methyl-4 (3H)-pyrimidinone, a promising new herbicide

EC Taylor, P Zhou, CM Tice, Z Lidert, RC Roemmele

Index: Taylor, Edward C.; Zhou, Ping; Tice, Colin M.; Lidert, Zev; Roemmele, Renee C. Tetrahedron Letters, 1997 , vol. 38, # 25 p. 4339 - 4342

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Citation Number: 15

Abstract

A novel synthesis of the promising new herbicide 2-(2, 6-dichloro-4-pyridyl)-3-propargyl-5- ethyl-6-methyl-4 (3H)-pyrimidinone (12) is reported which features (1) regioselective carbon, followed by nitrogen, dialkylation of an intermediate dianion, and (2) a tandem “one-pot” sequence of reactions involving sigmatropic sulfoxide elimination, lithium chloride-induced demethylation of a carbomethoxy grouping, decarboxylation, and isomerization/ ...