Binap, (A+-)- → 1-(1-{4-[7-(1-Ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-phenyl}-piperidin-4-yl)-ethanone

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-[4-(4-amino-phenyl)-piperazin-1-yl]-ethanone (70.5 mg, 0.32 mmol) and sodium tert-butoxide (38.4 mg, 0.4 mmol) in 1,4-dioxane (0.3 mL) are added a solution of 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine (60 mg, 0.26 mmol) in 1,4-dioxane (0.6 mL), Pd2(dba)3 (12.2 mg, 0.013 mmol) and BINAP (16.6 mg, 0.026 mmol). The mixture is degassed, and heated at 100° C. for 3 h. The mixture is cooled to room temperature, diluted with EtOAc, and filtered through a pad of Celite. The filtrate is concentrated under reduced pressure. The crude product is purified by preparative HPLC to give 84.9 mg of 1-(1-{4-[7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-phenyl}-piperidin-4-yl)-ethanone as a pale white solid.

Provenance & Evidence