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

HRID 1862269
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HRID 1862269 반응식
O.[F:2][C:3]1[C:21]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]([CH3:33])[C:23]2=[O:34])=[CH:20][C:6]([O:7][C:8]2[C:9]([O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[N:10][CH:11]=[N:12][CH:13]=2)=[C:5]([N+:35]([O-])=O)[CH:4]=1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:35][C:5]1[CH:4]=[C:3]([F:2])[C:21]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:30])([F:32])[F:31])[N:24]([CH3:33])[C:23]2=[O:34])=[CH:20][C:6]=1[O:7][C:8]1[C:9]([O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[N:10][CH:11]=[N:12][CH:13]=1
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참가 물질

6

반응물 2

HCID 962Water2회HCID 186192355-{4-Fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}-4-(methoxycarbonyl)methoxypyrimidine

생성물 1

HCID 186191775-{2-Amino-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-4-(methoxycarbonyl)methoxypyrimidine수율 85.1%

시약·촉매·용매 3

HCID 23925Iron촉매
HCID 176
Acetic Acid
용매
2회
HCID 8857Ethyl Acetate용매

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온도
35 °C

실험 절차

To a mixture of 0.4 g of an iron powder, 2 ml of acetic acid and 0.2 ml of water was added a solution of 0.393 g of 5-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}-4-(methoxycarbonyl)methoxypyrimidine in 1 ml of acetic acid and 2 ml of ethyl acetate dropwise. After completion of the addition, the mixture was stirred for 1 hour at room temperature, for 2 hours at 30-40° C. Water was added to the mixture, then, the mixture was filtrated through Celite, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, and saturated saline, dried over anhydrous magnesium sulfate, and concentrated. Then, the resulted residue was subjected to silica gel chromatography to obtain 0.315 g of 5-{2-amino-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-4-(methoxycarbonyl)methoxypyrimidine.

후처리

  1. additionAfter completion of the addition
  2. filtrationthe mixture was filtrated through Celite
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-010f442ded42420d9a7d5d1b5d0af09b
출처 데이터셋
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06537948B1

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