Dimethylformamide → HCID 86611044, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-1-[3-(2-Chloro-phenyl)-6-(2,4-difluoro-phenoxy)-1-(3-trimethylsilanyl-propoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol (50 mg, 0.2846 mmol), Boc-(L)-Valine (68 mg, 0.313 mmol), 4-dimethylaminopyridine (7 mg, 0.057 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarodiimide (60 mg, 0.313 mmol) in 4 mL DMF was stirred at room temperature for three days, then heated to 120° C. for four hours. The reaction mixture was cooled and partitioned between water and ethyl acetate. The organic layer was separate, washed with 0.5N aqueous HCl, saturated aqueous sodium bicarbonate and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed on silica (0% to 50% EtOAc in hexanes) to give 50 mg of (S)-2-tert-butoxycarbonylamino-3-methyl-butyric acid (S)-2-[3-(2-chloro-phenyl)-6-(2,4-difluoro-phenoxy)-1-methyl1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-1-methyl-ethyl ester

Provenance & Evidence