SRN1 mechanism in heteroaromatic nucleophilic substitution. Reactions involving halogenated pyrimidines, pyridazines, and pyrazines

DR Carver, AP Komin, JS Hubbard…

Index: Carver, David R.; Komin, Andrew P.; Hubbard, James S.; Wolfe, James S. Journal of Organic Chemistry, 1981 , vol. 46, # 2 p. 294 - 299

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Citation Number: 40

Abstract

Results Pyrimidines. Initial studies were focused on reactions of 2-chloropyrimidine (1) with the potassium enolates of acetone, pinacolone, and diisopropyl ketone. Results of these experiments are summarized in Scheme I1 and Table I. Photostimulated reaction of potassioacetone with 1 for 15 min afforded the expected ketone 2 in only 15% yield. The remainder of the product mixture consisted of 3 and intractable polymeric material. The ...