Water → 4-(1-(3-(Trifluoromethyl)phenyl)-3-methyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)benzonitrile

Participants

Reaction Steps

Lithium diisopropylamide (2.0 M in tetrahydrofuran, 265 μL, 0.53 mmol) is added at 0° C. to a solution of 4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-benzonitrile (example 1, 200 mg, 0.486 mmol) in N,N-dimethylformamide (10 mL). Methyl iodide (40 μL, 0.64 mmol) is added and the mixture is stirred for 1 h. Water is added and the mixture is extracted twice with dichloromethane. The combined organic layers are concentrated under reduced pressure, and the residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 50 mg; ESI mass spectrum [M+H]+=426; Retention time HPLC: 1.29 min (V001—006).

Provenance & Evidence