5-Bromouracil → 5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dione

HRID 1827925

Reaktionsgleichung

Reaktionsgleichung von HRID 1827925
[Br:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[F:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[C:24]=1[CH2:25]Br>ClC(Cl)C>[Br:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[N:6]([CH2:25][C:24]2[C:27]([C:31]([F:32])([F:34])[F:33])=[CH:28][CH:29]=[CH:30][C:23]=2[F:22])[CH:7]=1

Komponenten

5

Edukt 3

HCID 58025-BromouracilHCID 27375732-(Bromomethyl)-1-fluoro-3-(trifluoromethyl)benzeneHCID 6913588N,O-bis(trimethylsilyl)acetamide

Produkt 1

HCID 220645015-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dioneAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

A suspension of 5-bromouracil (31.0 g) in 300 mL of dichloroethane is treated with N,O-bis(trimethylsilyl)acetamide (80 mL). The reaction mixture is heated under nitrogen. The solution is cooled to ambient temperature, 2-fluoro-6-(trifluoromethyl)benzyl bromide (50 g) is added and the reaction mixture is heated overnight under the nitrogen. The reaction is cooled, quenched with MeOH, and partitioned between dichloromethane and water. The organic layer is washed with brine, dried (sodium sulfate), and evaporated to give a solid. The crude product is triturated with ether, filtered, and washed with ether three times providing 40.7 g of 5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dione 5a. MS (CI) m/z 366.0, 368.0 (MH+).

Aufarbeitung

  1. temperatureThe reaction mixture is heated under nitrogen
  2. temperaturethe reaction mixture is heated overnight under the nitrogen
  3. temperatureThe reaction is cooled
  4. customquenched with MeOH
  5. custompartitioned between dichloromethane and water
  6. washThe organic layer is washed with brine
  7. dry with materialdried (sodium sulfate)
  8. customevaporated
  9. customto give a solid
  10. customThe crude product is triturated with ether
  11. filtrationfiltered
  12. washwashed with ether three times

Quellen und Nachweise

ORD-Eintrag
ord-bbc1c3ebbfdb412c82b110ac7e42260c
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07056927B2

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