Dimethylformamide → HCID 68897683, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-(3-bromo-4-fluorophenyl)-8-[4-(trifluoromethoxy)phenyl]-2,3,4,8-tetrahydroimidazo[1,5-a]pyrimidin-6-ylamine (0.075 g, 0.159 mmol), 3-fluoro-5-(tributylstannyl)pyridine (0.092 g, 0.239 mmol), and dichlorobis(triphenylphosphine)palladium(II) (0.006 g, 0.008 mmol) in DMF is degassed, heated at 150° C. in a sealed tube for 1.5 h, cooled to room temperature and diluted with ethyl acetate (50 mL) and 5% aqueous LiCl. The reaction mixture is separated. The organic phase is washed with 5% aqueous LiCl, dried over sodium sulfate and concentrated. The resultant residue is purified by flash chromatography (silica, 95:5:0.25 methylene chloride/methanol/concentrated ammonium hydroxide as eluent) to afford the title product as a white solid, 0.043 g (56% yield), mp 94-105° C.; identified by NMR and mass spectral analyses. 1H NMR (300 MHz, CD3OD) 8.56 (d, J=1.3 Hz, 1H), 8.47 (d, J=2.6 Hz, 1H), 7.83 (d, J=9.7 Hz, 1H), 7.54-7.44 (m, 4H), 7.41-7.21 (m, 3H), 3.69 (m, 2H), 3.50 (m, 2H), 1.87 (m, 2H); ESI MS m/z 488 [C24H18F5N5O+H]+;

Provenance & Evidence