Cl[C:2]1[C:7]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:6][N:5]=[C:4]([CH3:19])[N:3]=1.CC([O-])=O.[Na+].C(O)C>[Pd].C1(C)C=CC=CC=1>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([S:8]([C:7]2[CH:6]=[N:5][C:4]([CH3:19])=[N:3][CH:2]=2)(=[O:9])=[O:10])=[CH:16][CH:15]=1A mixture of 4-chloro-5-(4-methoxy-benzenesulfonyl)-2-methylpyrimidine (468 mg, 1.57 mmol), prepared by the method described in example 1 part E, 10% Pd/C (50 mg), NaOAc (128 mg, 1.57 mmol), ethanol (5 mL) and toluene (15 mL) was hydrogenated at 40 psi (Parr Shaker Apparatus) overnight. The mixture was filtered through a pad of silica gel, and washed with EtOAc. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc) to provide 5-(4-methoxy-benzenesulfonyl)-2-methylpyrimidine (346 mg, 84%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 9.06 (s, 2H), 7.90 (d, J=9.9 Hz, 2H), 7.01 (d, J=9.9 Hz, 2H), 3.88 (s, 3H), 2.80 (s, 3H); ESI MS m/z 265 [(M+H)+, calcd for C12H13N2O3S, 265.1].
読み込み中…
