2-Chloro-5-phenyl-1,3,4-thiadiazole → 4-(2-(4-(5-Phenyl-1,3,4-thiadiazol-2-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-amine

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Reaction Steps

A slurry of pyridinium p-toluenesulfonate (0.18 g, 0.72 mmol), 4-(2-(4-aminophenoxy)pyridin-3-yl)pyrimidin-2-amine (0.100 g, 0.36 mmol), and 2-chloro-5-phenyl-1,3,4-thiadiazole (0.077 g, 0.39 mmol; prepared by method described in J. Med. Chem., 31:902 (1988)) was heated in 2 mL 2-BuOH in a sealed tube to 110° C. The reaction became dark brown and homogeneous. After 2 h the reaction was quenched with 1N NaOH and DCM. The aqueous layer was extracted 2×DCM, and the emulsified aqueous layer was filtered and rinsed with dichloromethane. The resulting solid was adsorbed onto silica gel from MeOH/DCM, dried, and purified by silica gel chromatography, 0-100% 90/10 DCM/MeOH in DCM to give 4-(2-(4-(5-phenyl-1,3,4-thiadiazol-2-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-amine as a white solid. MS m/z=440 [M+H]+. Calc'd for C23H17N7OS: 439.5.

Provenance & Evidence