2-[4-(4-Fluorophenoxy)phenyl]ethan-1-amine → HCID 178518127, compound

HRID 474870Notes

Reaction equation

CS[C:3]1[NH:4][CH:5]=[C:6]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[C:7](=[O:9])[N:8]=1.[F:17][C:18]1[CH:33]=[CH:32][C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH2:31])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1>C(O)C>[F:17][C:18]1[CH:33]=[CH:32][C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH:31][C:3]3[NH:4][CH:5]=[C:6]([CH2:10][C:11]4[CH:12]=[N:13][CH:14]=[N:15][CH:16]=4)[C:7](=[O:9])[N:8]=3)=[CH:25][CH:24]=2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 125 °C

Procedure

2-Methylsulfanyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (30 mg, 0.128 mmol, 1 eq) and 2-[4-(4-Fluoro-phenoxy)-phenyl]-ethylamine (44.4 mg, 0.192 mmol, 1.5 eq) were dissolved in dry ethanol (300 μl) and stirred at 125° C. for overnight. Reaction mixture was evaporated and crude residue was sent to HPLC/MS Purification. After HPLC/MS purification combined fractions of desired product were collected and put on lyophilisation to obtain 2-{2-[4-(4-fluoro-phenoxy)-phenyl]-ethylamino}-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (0.068 mmol; yield: 53.1%, HPLC-MS/UV: [M+H]+=418.45; rt: 9.78 min; purity: 98%). 1H NMR (300 MHz; DMSO-d6) δ/ppm 2.75 (t, J=7.50 Hz, 2H), 3.39-3.49 (m, 2H), 3.51 (s, 2H), 6.46 (br.s, 1H), 6.90 (d, J=8.57 Hz, 2H), 6.97-7.05 (m 2H), 7.15-7.25 (m, 4H), 7.66 (s, 1H), 8.66 (s, 2H), 8.97 (s, 1H), 10.92 (br.s., 1H)

Workup

customReaction mixture
customwas evaporated
customcrude residue was sent to HPLC/MS Purification
customAfter HPLC/MS purification
customwere collected

Sources & evidence

ORD record: ord-7400c84d4b8c49f1a1f6db6e7a2d9b98
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

Loading…