Methyl formate → HCID 46841270, compound

Participants

Reaction Steps

Methyl formate (10 mL, 162 mmol) was added to a solution of 3-(4-aminophenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one (0.200 g, 0.50 mmol) in EtOH (10 mL) and heated at reflux. More methyl formate (5 mL, 81 mmol) was added and the mixture was heated at reflux for 2 more days, before being concentrated in vacuo and purification by flash chromatography on silica gel eluting with 2% to 8% MeOH in CH2Cl2. Further purification was effected by reverse phase chromatography eluting with 10% to 90% CH3CN in H2O with 0.1% TFA. The desired fractions were collected, basified, extracted, and concentrated, to afford the title compound as a white solid (0.072 g, 33%). 1H-NMR (300 MHz, DMSO-d6, mixture of rotamers): δ 10.24 (s, 0.8H), 10.18 (m, 0.2H), 8.72-8.87 (m, 0.2H), 8.25 (d, J=1.7 Hz, 0.8H), 8.18 (dd, J=6.9, 1.1 Hz, 1H), 7.83-7.96 (m, 1H), 7.73 (d, J=8.0 Hz, 1H), 7.51-7.59 (m, 2.5H), 7.24 (d, J=8.7 Hz, 2H), 7.11-7.19 (m, 0.5H), 7.03 (s, 2H), 4.81 (t, J=5.4 Hz, 1H), 3.63-3.71 (m, 4H), 2.09 (s, 6H). MS (APCI) m/z: 430 (M+H)+.

Provenance & Evidence