2-[4-(3-Chloro-4-trifluoromethyl-phenoxy)-phenyl]-ethylamine → HCID 178494127, compound

Participants

Reaction Conditions

Reaction Steps

2-[4-(3-chloro-4-trifluoromethyl-phenoxy)-phenyl]-ethylamine (0.317 mmol, 1 eq) and 5-(2-methoxy-pyrimidin-5-ylmethyl)-2-methylsulfanyl-1H-pyrimidin-4-one (0.322 mmol, 0.95 eq) were dissolved in dry ethanol (300 μL) and stirred at 125° C. for 50 hours. Solvent was evaporated and crude product was purified on Biotage SP1 Snap Si 25; 25 ml/min in the gradient of MeOH in DCM: 0-10% in 25CV. The appropriate fractions were combined and evaporated in vacuo to give the required product 2-{2-[4-(3-chloro-4-trifluoromethyl-phenoxy)-phenyl]ethylamino}-5-(2-methoxy-pyrimidin-5-ylmethyl)-1H-pyrimidin-4-one (0.064 mmol, yield: 20%, UPLC-MS/UV: [M+H]+=517.97; rt: 11.53 mins; purity: 90%). 1H NMR (300 MHz; CDCl3) δ/ppm 2.92 (t, J=7.76, 2H), 3.51 (s, 2H), 3.59-3.70 (m, 2H), 3.94 (s, 3H), 5.33 (br.s., 1H), 6.86 (dd, J=9.07, J=2.01, 1H), 6.96-7.03 (m, 2H), 7.23-7.31 (m, 3H), 7.58 (d, J=8.82, 1H), 7.67 (s, 1H), 8.39 (s, 2H)

Provenance & Evidence