Reaction of ketone enolates with 2, 4-dichloropyrimidine. A novel pyrimidine to pyridine interconversion

…, DR Carver, JS Hubbard, YP Sachdeva…

Index: Bell, Harold M.; Carver, David R.; Hubbard, James S.; Sachdeva, Yesh P.; Wolfe, James F.; Greenwood, Thomas D. Journal of Organic Chemistry, 1985 , vol. 50, # 19 p. 3442 - 3444

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Citation Number: 7

Abstract

Treatment of 2, 4-dichloropyrimidine (1) with a series of ketone potassium enolates in liquid NH3 results in a novel ring transformation leading to the formation of 6-(cyanamino) pyridines (8a-c). An SN (ANRORC) mechanism initiated by nucleophilic addition of the enolate to C6 of 1 is proposed. The pyrimidine-pyridine transformation involves displacement of the N,-C2-N3 portion of pyrimidine with a CCN moiety, where the enolate ...