Hydrochloric Acid → 3-(7-(3-(Trifluoromethyl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid

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Reaction Steps

To a stirred solution of methyl 3-(7-(3-(trifluoromethyl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoate (100 mg, 0.23 mmol) in 3 mL of THF and 3 mL of methanol was added a solution of sodium hydroxide (46.5 mg, 1.16 mmol) in 1 mL of water at room temperature. Then the reaction mixture was stirred at room temperature for 16 hours. HCl was added until pH=4. The solvent was evaporated at 40° C. at reduced pressure and the residue was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with a mixture of petroleum ether and ethyl acetate (1:1)) to give 3-(7-(3-(trifluoromethyl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid (65 mg, 67.2%) as a pale yellow solid. 1H NMR (300 MHz, DMSO): δ 13.15 (brs, 1H), 10.65 (s, 1H), 9.46 (s, 1H), 9.00 (s, 1H), 8.67 (s, 1H), 8.60 (d, 1H, J=7.8 Hz), 8.26 (d, 1H, J=7.8 Hz), 8.10 (d, 1H, J=7.5 Hz), 7.68-7.63 (m, 2H), 7.49 (d, 1H, J=7.8 Hz). LC-MS: 417 [M+H]+, 415 [M−H]−, tR=1.65 min. HPLC: 95.14% at 214 nm, 95.28% at 254 nm, tR=7.71 min.

Provenance & Evidence