2-[4-(4-Fluoro-phenoxy)-phenyl]-ethyl-methyl amine → HCID 178483269, compound

HRID 474874Notes

Reaction equation

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

Participants

Conditions

Temperature: 125 °C

Procedure

2-[4-(4-fluoro-phenoxy)-phenyl]-ethyl-methyl amine (0.204 mmol, 1 eq) and 2-methylsulfanyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (0.082 mmol, 0.4 eq) were dissolved in dry ethanol (200 μL) and stirred at 125° C. for 16 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 30CV. The appropriate fractions were combined and evaporated in vacuo to give the required product 2-{2-[4-(4-fluoro-phenoxy)phenyl]-ethyl-methyl-amino}-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (0.042 mmol, yield: 20%, HPLC-MS/UV: [M+H]+=432.14; rt: 10.14 mins; purity: 97%). 1H NMR (300 MHz; CDCl3) δ/ppm 2.89 (t, J=7.17, 2H), 3.59 (s, 2H), 3.69-3.77 (m, 2H), 6.86-7.05 (m, 5H), 7.10-7.18 (m, 2H), 7.23-7.30 (m, 2H), 7.69 (s, 1H), 8.61 (s, 1H), 9.02-9.05 (m, 1H), 9.95 (br.s., 1H)

Workup

customSolvent was evaporated
customcrude product was purified on Biotage SP1 Snap Si 25
customevaporated in vacuo

Sources & evidence

ORD record: ord-6ad3b0d5840f4a568878af29314710db
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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