O-Toluidine → 4-(4-Methoxy-phenylsulfanyl)-3-(7-methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-N-o-tolyl-benzamide

Participants

Reaction Steps

To a solution of o-toluidine (0.208 mL, 1.94 mmol) in toluene (10 mL) was added AlMe3 (0.97 mL, 1.94 mmol) and the reaction mixture stirred for 30 minutes at room temperature. Then, the product from Example 148A (140 mg, 0.324 mmol) was added in one portion and the reaction mixture refluxed for 3 hours. The reaction mixture was cooled to room temperature and poured into a rapidly stirring solution of Rochelle's salt. After stirring the solution overnight at room temperature, the reaction was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over MgSO4, and concentrated under vacuum to a residue that was purified by silica gel chromatography using methanol in dichloromethane as eluent to provide the title compound (106 mg, 65%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 2.21 (s, 3H), 2.69 (s, 3H), 3.78 (s, 3H), 7.00 (d, J=8.82 Hz, 2H), 7.11-7.35 (m, 5H), 7.40 (d, J=8.82 Hz, 2H), 7.57 (d, J=8.46 Hz, 1H), 7.84 (d, J=6.99 Hz, 1H), 8.00 (s, 1H), 8.59 (s, 1H), 8.81 (d, J=8.09 Hz, 1H), 9.87 (s, 1H), 10.20 (s, 1H); MS (APCI) m/z 508 (M+H)+.

Provenance & Evidence