2-(4-(5-Trifluoromethyl-2-pyridinyloxy)phenyl)ethylamine → HCID 178494128, compound

HRID 474868Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH2:18])=[CH:12][CH:11]=2)=[N:7][CH:8]=1.[CH3:21][O:22][C:23]1[N:28]=[CH:27][C:26]([CH2:29][C:30]2[C:31](=[O:38])[N:32]=[C:33](SC)[NH:34][CH:35]=2)=[CH:25][N:24]=1>C(O)C>[CH3:21][O:22][C:23]1[N:24]=[CH:25][C:26]([CH2:29][C:30]2[C:31](=[O:38])[N:32]=[C:33]([NH:18][CH2:17][CH2:16][C:13]3[CH:14]=[CH:15][C:10]([O:9][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:1])[F:20])=[CH:8][N:7]=4)=[CH:11][CH:12]=3)[NH:34][CH:35]=2)=[CH:27][N:28]=1

Participants

Conditions

Temperature: 125 °C

Procedure

2-[4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl]ethylamine (0.246 mmol, 1.3 eq) and 5-(2-methoxy-pyrimidin-5-ylmethyl)-2-methylsulfanyl-1H-pyrimidin-4-one (0.189 mmol, 1 eq) were dissolved in dry ethanol (300 μL) and stirred at 125° C. for 16 hours. Solvent was evaporated and crude product was purified by Waters Mass Direct Autopurification system giving 5-(2-methoxy-pyrimidin-5-ylmethyl)-2-{2-[4-(5-trifluoromethyl-pyridin-2-yloxy)phenyl]-ethylamino}-1H-pyrimidin-4-one (0.090 mmol; yield: 36%, HPLC-MS/UV: [M+H]+=499.34; rt: 10.40 min; purity: 94%). 1H NMR (300 MHz; CDCl3) δ/ppm 2.93 (t, J=7.05, 2H), 3.51 (s, 2H), 3.58-3.74 (m, 2H), 3.95 (s, 1H), 5.31 (br.s., 1H), 6.98-7.13 (m, 3H), 7.22-7.32 (m, 2H), 7.61-7.67 (m, 1H), 7.89 (dd, J=8.50, J=2.64, 1H), 8.38 (m, 1H)

Workup

customSolvent was evaporated
customcrude product was purified by Waters Mass Direct Autopurification system

Sources & evidence

ORD record: ord-4e4610cd187444f0a1eb9afd64aa004e
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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