Diphosgene → (3-Chloro-phenyl)-methyl-carbamic Acid 4-trifluoromethyl-pyrimidin-2-yl Ester

反応式

[O:1]=[C:2](Cl)[O:3][C:4](Cl)(Cl)Cl.[F:9][C:10]([F:19])([F:18])[C:11]1[CH:16]=[CH:15][N:14]=C(O)[N:12]=1.[Cl:20][C:21]1[CH:22]=[C:23]([NH:27][CH3:28])[CH:24]=[CH:25][CH:26]=1>O1CCCC1>[F:9][C:10]([F:19])([F:18])[C:11]1[CH:16]=[CH:15][N:14]=[C:4]([O:3][C:2](=[O:1])[N:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([Cl:20])[CH:22]=2)[CH3:28])[N:12]=1

参加物

実験手順

At 0° C. diphosgene (0.99 g, 5.00 mmol) was added to a stirred solution of 4-trifluoromethyl-2-hydroxypyrimidine (1.64 g, 10.0 mmol) in tetrahydrofuran (25 ml). The cooling bath was removed and stirring was continued at room temperature for 1 hour. (3-Chlorophenyl)-methylamine (0.35 g, 2.50 mmol) was added to one-fourth of the solution. After stirring overnight at room temperature the solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (20:80)) followed by preparative HPLC, yielding the title compound (332 mg, 40%) as a colourless oil.