Cyanogen Bromide → 8-(3-Bromo-4-fluorophenyl)-8-[4-(trifluoromethoxy)phenyl]-2,3,4,8-tetrahydroimidazo[1,5-a]pyrimidin-6-ylamine

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A mixture of 1-(3-bromo-4-fluorophenyl)-1-(tetrahydropyrimidin-2-yl)-1-[4-(trifluoromethoxy)phenyl]methylamine (0.85 g, ˜80% purity, ˜1.52 mmol) and cyanogen bromide (0.81 g, 7.62 mmol) in acetonitrile is stirred at room temperature for 45 min, heated at 100° C. in a sealed tube overnight, cooled to room temperature 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 compound as a tan solid, 0.26 g (36% yield), identified by NMR and mass spectral analyses. 1H NMR (300 MHz, CDCl3) δ 7.74 (dd, J=6.7, 2.3 Hz, 1H), 7.49 (dd, J=6.7, 2.1 Hz, 2H), 7.38 (m, 1H), 7.13 (d, J=8.1 Hz, 2H), 7.03 (t, J=8.5 Hz, 1H), 3.58 (m, 4H), 1.86 (m, 2H); ESI MS m/z 471 [C19H15BrF4N4O+H]+.

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