Diisopropylethylamine → Ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate

反応式

Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=1.C(N(C(C)C)CC)(C)C>C(O)C.[Pd]>[F:16][C:13]([F:14])([F:15])[C:4]1[N:3]=[CH:2][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=1

参加物

実験手順

To a solution of ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate (30.2 g, 119.0 mmol) in ethanol (594 mL) under nitrogen were added palladium (10% on carbon, 50% water wet; 2.58 g, 1.21 mmol) and diisopropylethylamine (50.0 mL, 286.0 mmol). The mixture stirred under hydrogen (1 atm). After 6 h, the mixture was filtered with Celite. The filtrate was concentrated and ethyl acetate was added. The mixture was washed with saturated aqueous sodium bicarbonate (2×), saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated to give the title compound (25.6 g). MS 221.1 (M+1).