Trifluoroacetic acid → HCID 178486806, compound

Participants

Reaction Steps

5-(4-(6,7-Dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-3-methyl-2-methylthio-3H-pyrimidin-4-one (Step 1, 1.048 g, 2.3 mmol) was dissolved in CH3CN (15 mL) and TFA (1.7 mL) and cooled to 0° C. Urea hydrogen peroxide (290 mg, 3.09 mmol) was added, and the reaction was stirred for 5 min. trifluoroacetic anhydride (0.43 mL, 3.09 mmol) was added, and the reaction was warmed to RT and stirred for 40 min. The mixture was quenched with H2O (10 mL) and EtOAc (25 mL) and allowed to stand overnight. Saturated NaHCO3 (10 mL) and EtOAc were added, and the layers were separated. The aqueous layer was extracted with EtOAc, and the organic layers were combined, dried over Na2SO4, filtered, concentrated, and purified on silica gel (EtOAc→1:1 EtOAc/MeOH) to give title compound. MS (ESI pos. ion) m/z: 411. Calc'd for C21H17FN3O5: 410.39.

Provenance & Evidence