Cesium fluoride → 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-methyl-2-oxo-piperidin-3-yl)-amide

Participants

Reaction Steps

To a solution of 2-cyclopropyl-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-methyl-2-oxo-piperidin-3-yl)-amide (145 mg, 0.33 mmol) in acetonitrile (14.2 mL) at room temperature was added 18-crown-6 (86.4 mg, 0.33 mmol) and cesium fluoride (497 mg, 3.27 mmol). The reaction mixture was heated to reflux temperature for 48 h then cooled to room temperature and filtered over a pad of celite. The filtrate was evaporated under vacuum and the crude residue was partitioned between EtOAc (25 mL) and water (25 mL). The organic extract was dried (Na2SO4) and evaporated under vacuum. The crude residue was purified by SiO2 column chromatography (25 g, CH2Cl2/MeOH/NH4OH, 100:0:0 to 90:9.5:0.5) to give 60 mg (59%) of 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-methyl-2-oxo-piperidin-3-yl)-amide as a white solid. MS: (M+H)+=314.

Provenance & Evidence