1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidine-4-carboxylic acid [3-(4-fluoro-phenoxy)-phenyl]-amide → HCID 58694695, compound

Participants

Reaction Steps

A solution of 1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidine-4-carboxylic acid [3-(4-fluoro-phenoxy)-phenyl]-amide (52 mg, 0.12 mmol) in anhydrous THF (tetrahydrofuran) (10 mL) was cooled in an ice bath for 15 minutes with stirring. To this a solution of LAH (lithium aluminum hydride) in THF (1.0 M, 1.2 mL, 1.2 mmol) was added slowly. The reaction mixture was warmed to room temperature and stirred for 15 minutes, and then heated to reflux for 2 hours. The mixture was cooled to room temperature and then Na2SO4.10H2O was added until bubbling stopped. After stirring for 2 hours, the precipitate was filtered off and the filtrate concentrated. The residue was dissolved in acetonitrile (1.5 mL) and 30% aqueous TFA (trifluoroacetic acid) (0.5 mL), filtered, and chromatographed using reverse-phase high-pressure liquid chromatography. The clean fractions were pooled and concentrated and then lyophilized to remove water to yield [3-(4-fluoro-phenoxy)-phenyl]-[1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidin-4-ylmethyl]-amine as a white solid (7.9 mg, 15%, (M+H)+:432).

Provenance & Evidence