2,2,2-Trifluoroethanol → HCID 58223062, compound

Participants

Reaction Steps

To a solution of 2,4,6-trichloro-1,3,5-triazine (3 g) in acetone (70 mL) was added 2,2,2-trifluoroethanol (1.79 g) and 2,4,6-collidine (2.365 mL) in acetone (70.0 mL) dropwise over 1 hour. The resulting mixture was stirred at room temperature for 16 hours. All solvents were removed under vacuum to give a residue which was diluted with NMP (25 mL) and combined with methyl 4-aminobenzoate (2.71 g) and iPr2NEt (8.52 mL). After stirring at room temperature for 6 hours, methyl 4-(aminomethyl)benzoate hydrochloride (3.28 g) was added and the resulting mixture was stirred at room temperature for 16 hours. The mixture was diluted with water (300 mL) and extracted with EtOAc (2×400 mL). The organic layers were combined, washed with water (200 mL), brine (300 mL), dried over MgSO4 and concentrated. The residue was purified by recrystallization with MeOH to give methyl 4-(4-(4-(methoxycarbonyl)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (5 g).

Provenance & Evidence