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 28511노트

반응식

HRID 28511 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 866143135-(2-chloro-3-methoxyphenyl)-1-[1-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dione수율 88.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-7de01f8c58674d879b094db8cc6af7f9
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419983B2

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