2,4-Dichloro-5-nitropyrimidine → HCID 19021679, compound

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Reaction Steps

In Scheme A, reaction of 2,4-dichloro-5-nitropyrimidine (1) with lithium t-butoxide, cuprous iodide and ethylmagnesium bromide in THF at -78° C. gives 2-chloro-4-ethyl-5-nitropyrimidine (2). Displacement of the 2-chloro group in 2, is accomplished by treatment with 2-ethyl-4-methylimidazole or imidazole in acetonitrile at room temperature. Reduction of the nitro moiety in 3 to produce 4 is accomplished as illustrated. Reduction of 2,6-dichloro-4-ethyl-5-nitropyrimidine (5) is accomplished as illustrated to produce the compound 4 where R is hydrogen. ##STR6##

Provenance & Evidence