Sodium hydride → 4-Benzyloxy-3-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}pyridine

HRID 1862275노트

반응식

HRID 1862275 반응식
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[OH:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F[C:19]1[CH:24]=[C:23]([N:25]2[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]([CH3:36])[C:26]2=[O:37])[C:22]([F:38])=[CH:21][C:20]=1[N+:39]([O-:41])=[O:40].[Cl-].[NH4+]>CN(C)C=O>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[O:17][C:19]1[CH:24]=[C:23]([N:25]2[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[N:27]([CH3:36])[C:26]2=[O:37])[C:22]([F:38])=[CH:21][C:20]=1[N+:39]([O-:41])=[O:40])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 121155092,5-Difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzeneHCID 186192064-(Benzyloxy)pyridin-3-ol

생성물 1

HCID 186192594-Benzyloxy-3-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}pyridine수율 72.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 57 mg of sodium hydride and N,N-dimethylformamide, 0.286 g of 4-benzyloxy-3-hydroxypyridine was added and stirred at room temperature for 30 minutes. Then 0.5 g of 2,5-difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene was added to the mixture, and stirred for 1 hour at room temperature, then for 1 hour at 50-60° C. The mixture was poured into saturated ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated ammonium chloride solution and saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.548 g of 4-benzyloxy-3-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}pyridine.

후처리

  1. additionwas added
  2. stirringstirred for 1 hour at room temperature
  3. waitfor 1 hour at 50-60° C
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated ammonium chloride solution and saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ea067ac345054e90a60703b82ca66522
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06537948B1

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