Lithium Hydroxide → (2S)-2-Boc-aminomethyl-3-(4-chlorophenyl)-1-[4-(5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-pip-erazin-1-yl]-propan-1-one

Participants

Reaction Steps

To a solution of 7-Benzenesulfonyl-4-piperazin-1-yl-5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidine dihydrochloride (50 mg, 0.10 mmol), DIEA (0.10 mL, 0.60 mmol), and (2S)-2-(Boc-aminomethyl)-3-(4-chlorophenyl)-propionic acid (38 mg, 0.12 mmol) in 2 mL DCM was added HBTU (44 mg, 0.12 mmol). The reaction mixture was stirred at room temperature 2 hours, after which 2 mL MeOH and 0.5 mL 3M LiOH were added. The reaction mixture was heated to 35° C. and stirred 2 hours, after which saturated NaHCO3 was added, and the mixture was extracted with DCM. The combined extracts were dried (Na2SO4), filtered, and concentrated. The crude was purified on silica gel (flushed with 2:1 DCM:EtOAc, then gradient to 1:4 DCM:EtOAc) to give (2S)-2-Boc-aminomethyl-3-(4-chlorophenyl)-1-[4-(5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-pip-erazin-1-yl]-propan-1-one, which was used in the next step.

Provenance & Evidence