Cesium carbonate → HCID 86631157, compound

Participants

Reaction Steps

481 mg (1.48 mmol) of cesium carbonate were added to a solution of 135 mg (0.49 mmol) of ethyl (R)-8-amino-4-tert-butoxycarbonylaminooctanoate in 3.5 ml of dimethylformamide, and the mixture was stirred at room temperature. After 60 minutes, a solution of 87 mg (0.33 mmol) of 2-chloro-4,5-diphenylpyrimidine in 2.5 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 purified by a preparative HPLC (Purosphere, gradient acetonitrile/(water+0.5% TFA), gradient 20% acetonitrile to 100% in 30 minutes). 10 mg of ethyl (R)-4-tert-butoxycarbonylamino-8-(4,5-diphenylpyrimidin-2-ylamino)octanoate were obtained. The product obtained in this way was stirred with 50% trifluoroacetic acid for 2 hours, mixed with water and freeze dried. 12 mg (4%) of the desired product were obtained.

Provenance & Evidence