Cesium carbonate → HCID 68580921, compound

Participants

Reaction Steps

550 mg (1.69 mmol) of cesium carbonate were added to a solution of 161 mg (0.56 mmol) of (S)-3-(4-aminocyclohexyl)-2-tert-butoxycarbonylaminopropionic acid in 3 ml of dimethylformamide, and the mixture was stirred at room temperature. After 30 minutes, a solution of 100 mg (0.38 mmol) of 2-chloro-4,5-diphenylpyrimidine in 2 ml of dimethylformamide was added, and the mixture was stirred at 90° C. for 6 hours. The solvent was concentrated and the residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated under high vacuum. The residue was separated by a preparative HPLC (Purosphere, gradient acetonitrile/(water+0.5% TFA), gradient 20% acetonitrile to 100% in 30 minutes). 22 mg of (S)-2-tert-butoxycarbonylamino-3-[4-(4,5-diphenylpyrimidin-2-ylamino)cyclohexyl]propionic acid were obtained. The product obtained in this way was stirred with 50% trifluoroacetic acid in acetonitrile for 16 hours, mixed with water and freeze dried. 17 mg (11%) of the desired product were obtained.

Provenance & Evidence