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

HRID 1847069ノート

反応式

HRID 1847069 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

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 39871826(4R)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolaneHCID 667398036-Methoxypyrido[2,3-B]pyrazin-3(4H)-one

生成物 1

HCID 867249934-{2-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]ethyl}-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one収率 100.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

In N,N-dimethylformamide (40 ml) were dissolved 6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (1.48 g, 8.34 mmol) and (4R)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane (3.20 g, 12.51 mmol). Cesium carbonate (3.81 g, 11.68 mmol) was added to the solution and the mixture was stirred at 50° C. for 13 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 2.55 g (100%) of the title compound in the form of a light yellow 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-af4433c2f85a4e13beae1dd6783ded9d
出典データセット
uspto-grants-2015_02
特許番号
US08952010B2

反応ノート

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