Pyridine → Phenyl 4-(3-ethynylphenylamino)-7-fluoroquinazolin-6-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

N4-(3-ethynylphenyl)-7-fluoroquinazoline-4,6-diamine (50 mg, 0.18 mmol) was dissolved into DMF (2 mL) containing pyridine (17.5 μL, 0.21 mmol). Phenyl chloroformate (23 μL, 0.18 mmol) was added to the mixture at room temperature and stirred at 70° C. for 1 h to give phenyl 4-(3-ethynylphenylamino)-7-fluoroquinazolin-6-ylcarbamate. N1-(2,2-diethoxyethyl)-N2,N2-diethylethane-1,2-diamine (42 mg, 0.18 mmol) was added and stirred at 70° C. for 2.5 h. After cooled to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was concentrated and purified with a silica column to give 45 mg (70%) of 1-(2,2-diethoxyethyl)-1-(2-(diethylamino)ethyl)-3-(4-(3-ethynylphenylamino)-7-fluoroquinazolin-6-yl)urea.

Provenance & Evidence