tert-Butanol → Tert-butyl{2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}carbamate

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidine-5-carboxylic acid (307 mg), triethylamine (162 μL), and tert-butyl alcohol (9 mL) was added diphenylphosphorylazide (250 μL), followed by stirring at 90° C. for 7 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution (50 mL), followed by extraction with ethyl acetate (50 mL), and then the extract was washed with saturated brine (30 mL). The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain tert-butyl {2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}carbamate (270 mg) as a pale yellow powder.

Provenance & Evidence