Binap, (A+-)- → 1-{2-[4-(4-Acetyl-piperazin-1-yl)-phenylamino]-7-cyclopentyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-ethanone

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(2-Chloro-7-cyclopentyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-ethanone (40 mg, 0.144 mmol), 1-[4-(4-Amino-phenyl)-piperazin-1-yl]-ethanone (37.9 mg, 0.172 mmol), Pd2(dba)3 (6.7 mg, 0.007 mmol), BINAP (9.15 mg, 0.014 mmol) and NaOtBu (20.7 mg, 0.216 mmol) in 1,4-dioxane (4 mL) is degassed and back-filled with nitrogen three times. The reaction mixture is heated to 80° C. for 2 hours. After cooling to room temperature water is added and the reaction mixture is extracted with ethyl acetate three times. The organic layers are combined, washed with brine and dried over anhydrous sodium sulfate. The solvent is evaporated and the crude material is purified by preparative HPLC to provide 1-{2-[4-(4-Acetyl-piperazin-1-yl)-phenylamino]-7-cyclopentyl-5methyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-ethanone (16 mg, 24%). [M+H]+=461.13.

Provenance & Evidence