4-(4-chlorophenoxy)Benzeneethanamine → HCID 178518123, compound

Participants

Reaction Conditions

Reaction Steps

2-Methylsulfanyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (30 mg, 0.128 mmol, 1 eq) and 2-[4-(4-Chloro-phenoxy)-phenyl]-ethylamine (47.5 mg, 0.192 mmol, 1.5 eq) were dissolved in dry ethanol (300 μl) and stirred at 130° C. for overnight. Reaction mixture was evaporated and crude residue was purified via Biotage SP-1 Snap Si 10 g; 15 ml/min; UV Wavelength (Collection: 254 nm; Monitor: 290 nm) in the gradient of MeOH in DCM: 0% for 1 CV, 0-8% for 15 CV. The appropriate fractions were combined and product was triturated with cyclohexane to give 2-{2-[4-(4-Chloro-phenoxy)-phenyl]-ethylamino}-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (0.077 mmol; yield: 60.2%, HPLC-MS/UV: [M+H]+=434.90; rt: 10.52 min; purity: 95%). 1H NMR (300 MHz; DMSO-d6) δ/ppm 2.77 (t, J=7.12 Hz, 2H), 3.40-3.50 (m, 2H), 3.52 (s, 2H), 6.34 (br.s., 1H), 6.90-7.03 (m, 4H), 7.25 (d, J=7.63, 2H), 7.40 (d, J=8.65, 2H), 7.68 (s, 1H), 8.66 (s, 2H), 8.97 (s, 1H), 10.85 (br.s., 1H)

Provenance & Evidence