Hydrochloric Acid → HCID 66549329, compound

Participants

Reaction Steps

To a stirred solution of methyl 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)phenethyl)benzoate (70 mg, 0.13 mmol) in 3 mL of 1,4-dioxane and 3 mL of H2O was added NaOH (140 mg, 3.5 mmol) at room temperature. Then the reaction was stirred at room temperature overnight and then treated with conc. HCl until pH=3-4. The solvent was removed under reduced pressure, the residue was triturated with H2O (3×10 mL) and ethyl acetate (3×10 mL) then dried to give 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)phenethyl)benzoic acid (35 mg, 51%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 10.13 (s, 1H), 9.39 (s, 1H), 8.32-8.24 (m, 2H), 7.89-7.84 (m, 3H), 7.52-7.40 (m, 5H), 7.03 (d, 1H, J=8.7 Hz), 3.84 (s, 3H), 3.79 (s, 3H), 3.37 (brs, 4H). LC-MS: 513 [M+H]+, tR=1.67 min. HPLC: 97.30% at 214 nm, 97.09% at 254 nm, tR=5.16 min.

Provenance & Evidence