Water → HCID 57531498, compound

Participants

Reaction Conditions

Reaction Steps

To a flask containing LAH (132 mg, 3.0 eq., 3.18 mmol) in anhydrous THF (20 mL) is added 1-(2-(2,6-diethyl-phenyl)-6-methyl-5-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyrimidin-4-yl)-4-trimethylsilanyloxy-piperidine-4-carbonitrile 12 (0.63 g, 1.06 mmol) as a solution in THF (5 mL) over 10 min. The reaction is refluxed overnight. Following cooling to 0° C., water (0.132 mL) NaOH (15%, 0.132 mL) and water (0.396 mL) are added successively, followed by addition of EtOAc (100 mL) and MgSO4 (100 mg). The suspension is filtered through celite and the celite bed is washed with 20:1 EtOAc:MeOH (2×100 mL). Concentration affords the title compound as an off-white solid. [mass expected (527.74); mass found (527.27)].

Provenance & Evidence