2-[4-(3-Chloro-4-trifluoromethyl-phenoxy)-phenyl]-ethylamine → HCID 178432721, compound

Participants

Reaction Conditions

Reaction Steps

2-[4-(3-chloro-4-trifluoromethyl-phenoxy)-phenyl]-ethylamine (0.317 mmol, 1.01 eq) and 5-(2-methyl-pyrimidin-5-ylmethyl)-2-methylsulfanyl-1H-pyrimidin-4-one (0.322 mmol, 1 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 10; 15 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-methyl-pyrimidin-5-ylmethyl)-1H-pyrimidin-4-one (0.145 mmol, yield: 44%, HPLC-MS/UV:[M+H]+=517.97; rt: 11.53 mins; purity: 90%). 1H NMR (300 MHz; CDCl3) δ/ppm 2.65 (s, 3H), 2.92 (t, J=6.57, 2H), 3.53 (s, 2H), 3.57-3.69 (m, 2H), 5.39 (br.s., 1H), 7.01 (d, J=8.69, 1H), 7.08 (d, J=8.50 2H), 7.27-7.31 (m, 2H), 7.66 (s, 1H), 7.89 (dd, J=9.58, J=2.73, 1H), 8.36-8.42 (m, 1H), 8.51 (s, 2H), 11.21 (br.s., 1H)

Provenance & Evidence