Trifluoroacetic acid → 4-(3-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamido)benzoic acid

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tert-Butyl-4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamido)benzoate (45 mg, 0.077 mmol) in 10 mL of DCM was treated with TFA (2 mL) dropwise. The resulting yellow solution was stirred at ambient temperature overnight. The excess of solvent was removed under reduced pressure, the residue was triturated with n-hexane decanted, and dried to give 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamido)benzoic acid (27 mg, 66.4%). 1H NMR (300 MHz, DMSO): δ 12.80 (brs, 1H), 10.76 (s, 1H), 10.19 (s, 1H), 9.41 (s, 1H), 8.96 (s, 1H), 8.62 (d, 1H, J=7.8 Hz), 8.09 (d, 1H, J=7.8 Hz), 7.97 (s, 4H), 7.84 (s, 1H), 7.71 (t, 1H, J=7.7 Hz), 7.54 (dd, 1H, J1=8.7 Hz, J2=2.1 Hz), 6.99 (d, 1H, J=8.7 Hz), 3.81 (s, 3H), 3.74 (s, 3H). LC-MS: 528 [M+H]+, tR=1.54 min. HPLC: 96.02% at 214 nm, 95.94% at 254 nm, tR=6.62 min.

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