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

HRID 1744289

반응식

HRID 1744289 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 220645015-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dione수율 68.3%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

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 1a. MS (CI) m/z 366.0, 368.0 (MH+).

후처리

  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

출처 및 근거

ORD 기록
ord-fb255c2e1c9848e29c2f483cdc29cdde
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015226B2

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