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Water → 4-{2-[(4S)-2,2-Dimethyl-1,3-dioxolan-4yl]ethyl}-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847063
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HRID 1847063 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]=2[N:13]=1.I[CH2:15][CH2:16][C@H:17]1[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH3:22][C:19]1([CH3:23])[O:18][C@@H:17]([CH2:16][CH2:15][N:8]2[C:9](=[O:12])[CH:10]=[N:11][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[N:13][C:7]2=3)[CH2:21][O:20]1
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참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11076039(4S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolaneHCID 667398036-Methoxypyrido[2,3-B]pyrazin-3(4H)-one

생성물 1

HCID 867249884-{2-[(4S)-2,2-Dimethyl-1,3-dioxolan-4yl]ethyl}-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one수율 90.2%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
50 °C

실험 절차

In N,N-dimethylformamide (400 ml) were dissolved 6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (14.53 g, 82.00 mmol) and (4S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane (23.10 g, 90.20 mmol). Cesium carbonate (34.7 g, 1.06.6 mmol) was added to the solution and the mixture was stirred at 50° C. for 11 hours. After cooling in the air, water was added to the reaction solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 22.58 g (90%) of the title compound in the form of a yellow orange oily product.

후처리

  1. additionwas added to the reaction solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-c282702056b4447d822addf48c0fef1f
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952010B2

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