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 1862275ノート

反応式

HRID 1862275 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ea067ac345054e90a60703b82ca66522
出典データセット
uspto-grants-2003_03
特許番号
US06537948B1

反応ノート

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