Diisopropylethylamine → 3-(5-cyano-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidin-2-ylamino)-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To the reaction mixture of 3-(2-chloro-5-cyanopyrimidin-4-ylamino)-N-methylbenzamide and 3-(4-chloro-5-cyanopyrimidin-2-ylamino)-N-methylbenzamide (172.7 mg, 0.600 mmol) and 3-(4-fluorophenoxy)azetidine hydrochloride (128 mg, 0.631 mmol) in a disposable sealed tube at RT was added 2-propanol (4 mL) followed by N,N-diisopropylethylamine (0.314 mL, 1.802 mmol). The resulting reaction mixture was heated to 84° C. for 4.5 h, cooled to RT, concentrated, adsorbed onto silica gel, purified using MPLC (25 g cartridge about 20% full, 40 g column, 0 to 80% 90/10 CH2Cl2-MeOH in CH2Cl2) giving 3-(5-cyano-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidin-2-ylamino)-N-methylbenzamide (19.3 mg) and 3-(5-cyano-2-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidin-4-ylamino)-N-methylbenzamide (13.2 mg).

Provenance & Evidence