1,3-Propanediamine, N1,N1,N3-trimethyl- → 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, (0.050 g, 0.089 mmol) was dissolved in THF (5 mL) and N,N,N′-trimethyl-1,3-propanediamine (0.054 g, 0.44 mmol) was added. The mixture was stirred under argon at room temperature for 3 h. The reaction was not complete, so additional N,N,N′-trimethyl-1,3-propanediamine (0.108 g, 0.88 mmol) was added and the mixture stirred at room temperature for an additional 17 h, followed by heating to 400 C for 1 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 6:1:0.05, CH2Cl2:isopropanol:NH4OH to give the title compound as a white amorphous solid. mp 124-127° C.; LC-MS m/z 600 (M+H)+, 1.84 min (ret. time).

Provenance & Evidence