Water → 3-Amino-6-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-benzyloxypyridine

HRID 1862326ノート

反応式

HRID 1862326 の反応式
O.[Cl:2][C:3]1[CH:26]=[C:25]([F:27])[C:24]([N:28]2[C:33](=[O:34])[CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[N:30]([CH3:39])[C:29]2=[O:40])=[CH:23][C:4]=1[O:5][C:6]1[N:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([N+:20]([O-])=O)=[CH:8][CH:7]=1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:20][C:9]1[C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[N:11][C:6]([O:5][C:4]2[CH:23]=[C:24]([N:28]3[C:33](=[O:34])[CH:32]=[C:31]([C:35]([F:38])([F:36])[F:37])[N:30]([CH3:39])[C:29]3=[O:40])[C:25]([F:27])=[CH:26][C:3]=2[Cl:2])=[CH:7][CH:8]=1

参加物

6

反応物 2

HCID 962WaterHCID 186191896-{2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-benzyloxy-3-nitropyridine

生成物 1

HCID 186191973-Amino-6-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-benzyloxypyridine収率 89.7%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 176Acetic Acid溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
35 °C

実験手順

To a mixed solution of 3.0 g of an iron powder, 15 ml of acetic acid and 1.5 ml of water was added a solution of 3.0 g of 6-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-benzyloxy-3-nitropyridine in 10 ml of acetic acid and 10 ml of ethyl acetate dropwise while maintaining the temperature of the reaction solution at 35° C. or lower. After completion of the addition, the mixture was stirred over night, then, the reaction solution was filtrated through Celite, and the solvent was removed at reduced pressure. The residue was diluted with saturated aqueous sodium bicarbonate solution, extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The resulted residue was subjected to silica gel chromatography to obtain 2.55 g of 3-amino-6-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-benzyloxypyridine

後処理

  1. additionAfter completion of the addition
  2. filtrationthe reaction solution was filtrated through Celite
  3. customthe solvent was removed at reduced pressure
  4. additionThe residue was diluted with saturated aqueous sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-4cdc7046e771452da8b3cb55bc9afa4b
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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