1,4-Dioxane hydrochloride → N2-(3-chlorophenyl)-4-(trifluoromethyl)pyrimidine-2,5-diamine

Participants

Reaction Steps

To a mixture of tert-butyl{2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}carbamate (267 mg) and 1,4-dioxane (3 mL) was added a 4 M hydrogen chloride-1,4-dioxane solution (3 mL), followed by stirring at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, and to the obtained residue was added a saturated aqueous sodium hydrogen carbonate solution (20 mL), followed by extraction with ethyl acetate (50 mL). The extract was washed with saturated brine (20 mL), and the organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol) to obtain N2-(3-chlorophenyl)-4-(trifluoromethyl)pyrimidine-2,5-diamine (180 mg) as a yellow solid.

Provenance & Evidence