1-(Bromomethyl)-2-fluoro-3-(trifluoromethyl)benzene → 5-(2-chloro-3-methoxyphenyl)-1-[1-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dione

HRID 28511Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 28511
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[C:11](=[O:17])[NH:12][C:13](=[O:16])[NH:14][CH:15]=1.[CH3:18][Si](C([Si](C)(C)C)C(N)=O)(C)C.[F:30][C:31]1[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:36]=[CH:35][C:32]=1CBr>C(#N)C>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[C:11](=[O:17])[NH:12][C:13](=[O:16])[N:14]([CH2:18][C:31]2([F:30])[C:38]([C:39]([F:40])([F:41])[F:42])=[CH:37][CH:36]=[CH:35][CH2:32]2)[CH:15]=1

Komponenten

5

Edukt 3

HCID 27375691-(Bromomethyl)-2-fluoro-3-(trifluoromethyl)benzeneHCID 11708267BistrimethylsilylacetamidHCID 220378355-(2-chloro-3-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 866143135-(2-chloro-3-methoxyphenyl)-1-[1-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dioneAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a suspension of 5-(2-chloro-3-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione 7e (2.2 g, 8.7 mmol) in acetonitrile (25 mL) was added bis(trimethylsilyl)acetamide (4.3 mL, 17.4 mmol), and the resulting solution was refluxed for 1.5 hours. The mixture was cooled to room temperature, 2-fluoro-3-trifluoromethylbenzyl bromide (2.7 g, 10.5 mmol) was added, and reflux was resumed for 16 hours. The reaction was quenched by addition of MeOH (25 mL) and stirring for 2 hours. After concentration, the residue was purified by column chromatography on silica gel with ethyl acetate/hexanes 1/1 to afford 5-(2-chloro-3-methoxyphenyl)-1-[1-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dione 7f (3.3 g, 88%) as a white solid. MS (CI) m/z 429.0, 431.0 (MH+).

Aufarbeitung

  1. temperaturethe resulting solution was refluxed for 1.5 hours
  2. temperaturereflux
  3. customThe reaction was quenched by addition of MeOH (25 mL)
  4. concentrationAfter concentration
  5. customthe residue was purified by column chromatography on silica gel with ethyl acetate/hexanes 1/1

Quellen und Nachweise

ORD-Eintrag
ord-7de01f8c58674d879b094db8cc6af7f9
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419983B2

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