Sodium Iodide → 1-[[2-Fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methylpyrimidine-2,4-dione

HRID 28493

반응식

HRID 28493 반응식
[Na+].[I-].[F:3][C:4]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[C:5]=1[CH2:6][NH:7][C:8]([NH2:10])=[O:9].[CH2:19]=[C:20]1O[C:22](=[O:23])[CH2:21]1.C[Si](Cl)(C)C>C(#N)C.O>[F:3][C:4]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[C:5]=1[CH2:6][N:7]1[C:20]([CH3:19])=[CH:21][C:22](=[O:23])[NH:10][C:8]1=[O:9]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 12661DiketeneHCID 22037856N-(2-Fluoro-6-(trifluoromethyl)benzyl)urea

생성물 1

HCID 220378661-[[2-Fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methylpyrimidine-2,4-dione수율 81.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

NaI (43.9 g, 293 mmol) was added to N-[2-fluoro-6-(trifluoromethyl)benzyl]urea 1b (46.2 g, 19.6 mmol) in 365 mL of acetonitrile. The resulting mixture was cooled in an ice-water bath. Diketene (22.5 mL, 293 mmol) was added slowly via dropping funnel followed by addition of TMSCl (37.2 mL, 293 mmol) in the same manner. The resulting yellow suspension was allowed to warm to room temperature slowly and was stirred for 20 hours. LC-MS showed the disappearance of starting material. To the yellow mixture 525 mL of water was added and stirred overnight. After another 20 hours stirring, the precipitate was filtered via Buchnner funnel and the yellow solid was washed with water and EtOAc to give 1c as a white solid (48.5 g, 16 mmol). 1H NMR (CDCl3) δ 2.15 (s, 3H), 5.37 (s, 2H), 5.60 (s, 1H), 7.23-7.56 (m, 3H), 9.02 (s, 1H); MS (CI) m/z 303.0 (MH+).

후처리

  1. temperatureThe resulting mixture was cooled in an ice-water bath
  2. stirringstirred overnight
  3. stirringAfter another 20 hours stirring
  4. filtrationthe precipitate was filtered via Buchnner funnel
  5. washthe yellow solid was washed with water and EtOAc

출처 및 근거

ORD 기록
ord-c91028e2b11544319044cb0d1010dccd
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419983B2

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