Methanol → 2-Methylsulfanyl-4-(2-(phenylamino)phenylamino)pyrimidine-5-carboxylic acid (4-fluorophenyl)amide

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Reaction Steps

To a mixture of 4-chloro-2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (100 mg, 0.34 mmol) in dichloromethane (10 mL) was added N-phenyl-benzene-1,2-diamine (148 mg, 0.4 mmol) followed by N-methylmorpholine-bound resin (300 mg). The mixture was stirred at an ambient temperature for 16 h and was then heated at reflux for an additional 2 h. Methanol (5 mL) was added and the mixture was stirred at an ambient temperature for 40 h. The mixture was filtered through a plug of celite and the filter plug was washed with hot ethyl acetate (25 mL). The resulting solution was treated with hexanes to precipitate 70 mg (0.16 mmol, 47% yield) of the titled compound as a purple-red solid. 1H NMR (300 MHz, DMSO-d6) δ 10.64 (s, 1H), 10.29 (s, 1H), 8.74 (s, 1H), 8.10 (m, 1H), 7.58 (m, 3H), 7.25–7.05 (m, 7H), 6.79–6.679(m, 3H), 2.5(s, 3H); MS (EI) m/z 444.05 (M−H)−.

Provenance & Evidence