Hydrochloric Acid → 3'-{[4-(Trifluoromethyl)pyrimidin-2-yl]amino}biphenyl-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Lithium hydroxide (2 M, 0.374 mL, 0.749 mmol) was added to a solution of ethyl 3′-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}biphenyl-4-carboxylate in THF (1.99 mL) and methanol (0.99 mL) at room temperature, and then the mixture was heated at 45° C. for 6 hours. The reaction mixture was cooled to room temperature, neutralized with 10% aqueous HCl, diluted with brine, extracted with ethyl acetate (2×), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes+0.1% AcOH) to afford 3′-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}biphenyl-4-carboxylic acid as an off-white solid MS ESI calc'd. for C18H13F3N3O2 [M+H]+ 360, found 360. 1H NMR (500 MHz, CD3OD): δ 8.74 (s, 1H); 8.17 (s, 1H); 8.12 (d, J=7.9 Hz, 2H); 7.81-7.73 (m, 3H); 7.45 (t, J=7.9 Hz, 1H); 7.42-7.36 (m, 1H); 7.15 (d, J=4.5 Hz, 1H).

Provenance & Evidence