1-(4-methoxyphenyl)-N-methylmethanamine → N-(4-methoxybenzyl)-N,7-dimethyl-5-(1-methyl-1H-pyrazol-4-yl)imidazo[5,1-f][1,2,4]triazin-4-amine

Participants

Reaction Steps

The product was synthesized in a manner similar to that described for the preparation of 4-(azetidin-1-yl)-7-methyl-5-(1-methyl-1H-pyrazol-4-yl)imidazo[5,1-f][1,2,4]triazine in Example 2, except that 1-(4-methoxyphenyl)-N-methylmethanamine was utilized in place of azetidine hydrochloride, and the workup was modified somewhat: after the slurry was extracted with dichloromethane, the combined organic layers were washed with 1 N aqueous sodium hydroxide solution, washed with saturated aqueous sodium chloride solution, and dried over sodium sulfate. After filtration, the filtrate was concentrated in vacuo and passed through a short column of silica gel (Eluant: 5% methanol in ethyl acetate). The eluant was concentrated under reduced pressure, and the resulting solid was washed with tert-butyl methyl ether followed by diethyl ether, to provide C6. Yield: 36.0 g, 99.1 mmol, 76%. LCMS m/z 364.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.67 (s, 3H), 2.84 (s, 3H), 3.77 (s, 3H), 3.88 (s, 3H), 4.66 (s, 2H), 6.82 (br d, J=8.7 Hz, 2H), 7.07 (br d, J=8.6 Hz, 2H), 7.58 (s, 1H), 7.62 (s, 1H), 7.89 (s, 1H).

Provenance & Evidence