Potassium Carbonate → 3-[2(R)-{ethoxycarbonylpropyl-amino}-2-(isobutyl)ethyl]-5-(2-chloro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dione

HRID 28515

Reaktionsgleichung

[NH2:1][C@H:2]([CH2:33][CH:34]([CH3:36])[CH3:35])[CH2:3][N:4]1[C:9](=[O:10])[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:12]=2[Cl:19])=[CH:7][N:6]([CH2:20][C:21]2[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][C:22]=2[F:31])[C:5]1=[O:32].C([O-])([O-])=O.[K+].[K+].Br[CH2:44][CH2:45][CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48]>CN(C=O)C>[CH2:50]([O:49][C:47]([CH2:46][CH2:45][CH2:44][NH:1][C@H:2]([CH2:33][CH:34]([CH3:36])[CH3:35])[CH2:3][N:4]1[C:9](=[O:10])[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:12]=2[Cl:19])=[CH:7][N:6]([CH2:20][C:21]2[C:26]([C:27]([F:28])([F:30])[F:29])=[CH:25][CH:24]=[CH:23][C:22]=2[F:31])[C:5]1=[O:32])=[O:48])[CH3:51]

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

To a solution of compound 8b (25 mg, 0.048 mmol) in DMF (1 mL) was added K2CO3 (21 mg, 0.15 mmol) followed by ethyl 4-bromobutyrate (0.015 mL, 0.1 mmol). The mixture was heated at 95° C. for 16 hours, cooled to room temperature, and partitioned between ethyl acetate and H2O. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel with ethyl acetate/hexanes/triethylamine 500/500/5 to afford compound 8c . MS (CI) m/z 642.2, 644.2 (MH+).

Aufarbeitung

temperaturecooled to room temperature
custompartitioned between ethyl acetate and H2O
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel with ethyl acetate/hexanes/triethylamine 500/500/5

Quellen und Nachweise

ORD-Eintrag: ord-102ad2e526e94926a79af27b08f76779
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07419983B2

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