4-Amino-1-methylpiperidine → Ammonium Hydroxide

Participants

Reaction Steps

The compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(phenylmethyl)benzamide, (0.06 g, 0.106 mmol) was dissolved in CH2Cl2 (5 mL) and 4-amino-1-methylpiperidine (0.031 g, 0.265 mmol) was added. The mixture was stirred under argon at room temperature for 16 h with some product formation. The reaction was not complete, so additional 4-amino-1-methylpiperidine (0.031 g, 0.265 mmol) was added and the mixture stirred for an additional 24 h. The reaction still was not complete, and was then heated to reflux for 24 h. The solvents were pumped off in vacuo. The residue was taken up in EtOAc washed with 1M NaOH (2×), brine (1×), dried over anhydrous Na2SO4, filtered and evaporated The residue was flash chromatographed on silica gel (20 g) eluted with 6:2:0.2, CH2Cl2:ethanol:NH4OH to give the title compound as a white amorphous solid. mp (dec) 152-154° C.; LC-MS m/z 598 (M+H)+, 1.62 min (ret. time).

Provenance & Evidence