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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
ノート
印刷プレビュー

反応式

HRID 1847063 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c282702056b4447d822addf48c0fef1f
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08952010B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート