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

HRID 28513

Reaktionsgleichung

Reaktionsgleichung von HRID 28513
[NH2:1][C@H:2]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[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.[Na+].[Na+].Br[CH2:46][CH2:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50]>CN(C=O)C>[CH2:52]([O:51][C:49]([CH2:48][CH2:47][CH2:46][NH:1][C@H:2]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[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:50])[CH3:53]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 11376252(R)-1-(2-fluoro-6-(trifluoromethyl)benzyl)-3-(2-amino-2-phenylethyl)-5-(2-chloro-3-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 865965103-[2(R)-{ethoxycarbonylpropyl-amino}-2-phenylethyl]-5-(2-chloro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dioneAusbeute 53,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a solution of compound 7h (2.0 g, 3.65 mmol) in DMF (8 mL) was added Na2CO3 (0.47 g, 4.38 mmol) followed by ethyl 4-bromobutyrate (0.83 mL, 5.48 mmol). The mixture was heated at 95° C. for 1.5 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 7i (1.29 g) as a white solid. MS (CI) m/z 662.2, 664.2 (MH+)

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-d0fc61949e4c4ac1b1d8d452feff5a9a
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419983B2

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