Imidazole → HCID 13424620, compound

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Reaction Steps

A solution of 2.7 g (0.041 mol) of imidazole in 50 ml of dry tetrahydrofuran is treated at 0° C. with 1.8 g (0.041 mol) of 55 to 60 percent sodium hydride. After the hydrogen formation has finished, 3.8 g (0.041 mol) of methyl chloroformate in 20 ml of dry tetrahydrofuran are added dropwise at 0° C., whereupon the suspension obtained is treated dropwise at 0° with a solution of 2.9 g (0.021 mol) of 6-chloro-2,4-diaminopyrimidine and 4.5 g (0.041 mol) of potassium t-butylate in 30 ml of dry dimethylformamide. The mixture is stirred at 0° for 1 hour and then at 50° for 3 hours, whereupon 3 ml of methanol are added thereto and the solvent is evaporated to the largest extent possible. The residue is poured into ice-cold water, adjusted with 1N hydrochloric acid to pH 2 and extracted with methylene chloride and a small amount of methanol. After drying the organic extract over magnesium sulphate and evaporation under vacuum, the residue is recrystallized from ethyl acetate, there being obtained pure dimethyl 6-chloro-2,4-pyrimidinedicarbamate.

Provenance & Evidence