Triethylamine → HCID 135873239, compound

Participants

Reaction Steps

A mixture of 4-fluorophenylisocyanate (0.138 mL, 1.14 mmol), Et3N (0.185 mL, 1.32 mmol) and 4 (0.0700 g, 0.189 mmol) in THF (1.00 mL) was heated at reflux for 8 hours. The mixture was cooled, diluted with EtOAc (200 mL), washed with saturated aqueous NH4Cl (3×75 mL), brine (75 mL), dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified on silica gel (12 g, CH2Cl2/MeOH) and the product was freeze-dried from MeCN/H2O to provide 2-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenoxy)ethyl 4-fluoro-phenylcarbamate (5) (0.0710 g, 74%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 11.83 (s, 1H), 9.78 (s, 1H), 7.91 (s, 2H), 7.54-7.44 (m, 2H), 7.18-7.08 (m, 2H), 6.73 (d, J=2.31 Hz, 1H), 6.51 (d, J=2.31 Hz, 1H), 4.47-4.38 (m, 2H), 4.12-4.03 (m, 2H), 3.89 (s, 3H), 3.84 (s, 3H), 2.31 (s, 6H); MS (APCI) m/z 508 [C27H26FN3O6+H]+.

Provenance & Evidence