Hydrochloric Acid → 4-(2-(6-Chloro-2-methylpyrimidin-4-ylamino)thiazol-5-ylthio)picolinic acid

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Reaction Steps

To a stirring solution of methyl 4-(2-(6-chloro-2-methylpyrimidin-4-ylamino)thiazol-5-ylthio)picolinate (292 mg, 0.741 mmol) in THF (8 mL) was added NaOH (8 mL, 1M in water). After 6 h, the reaction was acidified with 10% HCl to pH ˜6 at which time a solid precipitated. The solid was collected by filtration, washed with water and allowed to dry overnight to give the title material (239 mg, 85%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 12.55 (1H, s), 8.33 (1H, d, J=5.31 Hz), 7.84 (1H, s), 7.57 (1H, d, J=1.77 Hz), 7.16 (1H, dd, J=5.31, 2.02 Hz), 6.90 (1H, s), 2.51 (3H, s). LC/MS (M+H)+: 380, 382. HPLC ret. time (Condition I): 1.175 min.

Provenance & Evidence