2-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamine → HCID 178518124, compound

Participants

Reaction Conditions

Reaction Steps

2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamine (0.317 mmol, 1.0 eq) and 5-(6-chloro-pyridin-3-ylmethyl)-2-methylsulfanyl-1H-pyrimidin-4-one (0.190 mmol, 0.6 eq) were dissolved in dry ethanol (300 μL) and stirred at 130° C. overnight. Solvent was evaporated and crude product was purified on Biotage SP1 Snap Si 10; 15 ml/min in the gradient of MeOH in DCM: 0-7% in 15 CV. The appropriate fractions were combined and evaporated in vacuo to give the required product 5-(6-chloro-pyridin-3-ylmethyl)-2-{2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamino}-1H-pyrimidin-4-one (0.084 mmol, yield: 26%, HPLC-MS/UV:[M+H]+=536.33; rt: 1.24 mins; purity: 95%). 1H NMR (300 MHz; CDCl3) δ/ppm 2.89 (t, J=7.17, 2H), 3.57 (s, 2H), 3.59-3.66 (m, 2H), 5.23 (br.s., 1H), 6.95 (dd, J=8.51, J=9.86, 2H), 7.03 (dd, J=9.41 J=2.24, 1H), 7.17-7.23 (m, 3H), 7.27-7.30 (m, 2H), 7.39 (dd, J=9.07, J=8.31, 1H), 7.47 (dd, J=8.06, J=2.51, 1H), 7.65 (s, 1H), 8.28 (d, J=2.26, 1H), 12.01 (br.s., 1H)

Provenance & Evidence