Potassium Iodide → 3-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-(2-piperidin-1-yl-pyrimidin-4-ylamino)-propionic acid

Participants

Reaction Conditions

Reaction Steps

3-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-(2-chloro-pyrimidin-4-ylamino)-propionic acid ethyl ester. To solution of 2-Amino-3-{4-[5-(4-tert-butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluorophenyl}propionic acid ethyl ester in DMF (20 mL) were added sodium carbonate (360 mg, 3.4 mmol), potassium iodide (10 mg), TBAB (10 mg), and 2,4-dichloro-pyrimidine (503 mg, 3.4 mmol). The mixture was heated at 50° C. for 4 hrs. The mixture was cooled to room temperature and partitioned between ethyl acetate and water. The combined organic layers were washed with brine, dried over sodium sulfate, filtrated, concentrated, and purified by chromatography to give the title compound (96 mg).

Provenance & Evidence