Ethyl Acetate → (S)-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-phenyl-acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a mixture of (S)-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl-acetic acid methyl ester (110 mg, 0.35 mmol) and (1,4-dimethyl-1H-indol-3-ylmethyl)-trimethylammonium iodide (180 mg, 0.52 mmol) in DMF (2.5 mL) is added K2CO3 (150 mg, 1.09 mmol). The mixture is stirred at 60° C. for 4 hours. The reaction mixture is allowed to cool to room temperature, dilutes with EtOAc (50 mL) and is washed with H2O (50 mL×3). The organic layer is dried over sodium sulfate and is concentrated. The resulting residue is purified by flash chromatography with 50% EtOAc in hexanes as the eluent to afford (S)-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-phenyl-acetic acid methyl ester (100 mg, 60%).

Provenance & Evidence