Lithium Hydroxide → 3-Boc-amino-2-(4-chlorophenyl)-1-[4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one

Participants

Reaction Steps

To a solution of 7-benzenesulfonyl-5-methyl-4-piperazin-1-yl-7H-pyrrolo[2,3-d]pyrimidine dihydrochloride (35 mg. 0.081 mmol), 3-Boc-amino-2-(4-chlorophenyl)-propionic acid (27 mg, 0.089 mmol), and TEA (0.11 mL, 0.81 mmol) 1.2 mL DCM was added HBTU (34 mg, 0.089 mmol). The reaction mixture was stirred at room temperature 2 hours, after which 0.15 mL 3M LiOH and 1.0 mL MeOH were added. The reaction mixture was stirred at 35° C. for 3.5 hours, after which saturated NaHCO3 was added. The mixture was extracted with DCM, and the combined extracts were dried (Na2SO4), filtered, and concentrated. The crude was purified on silica gel (flushed with 1:1 DCM:EtOAc, then gradient to 1:4 DCM:EtOAc) to give 3-Boc-amino-2-(4-chlorophenyl)-1-[4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one, which was used in the next step.

Provenance & Evidence