2-Methoxyethanol → 3-(2-Methoxyethoxy)-5-bromopyrazin-2-amine

HRID 69945

反応式

HRID 69945 の反応式
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][OH:7].Br[C:9]1[C:10]([NH2:16])=[N:11][CH:12]=[C:13]([Br:15])[N:14]=1>C1COCC1>[Br:15][C:13]1[N:14]=[C:9]([O:7][CH2:6][CH2:5][O:4][CH3:3])[C:10]([NH2:16])=[N:11][CH:12]=1

参加物

5

反応物 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 6200042-Amino-3,5-dibromopyrazine

生成物 1

HCID 592520723-(2-Methoxyethoxy)-5-bromopyrazin-2-amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A flame-dried round bottom flask was charged with a suspension of 95% NaH (1.3 eq) in anhydrous THF (0.2 M). The stirring mixture was cooled to 0° C. in an ice-water bath and 2-methoxyethanol (1.2 eq) was added drop wise via syringe. After 30 min 3,5-dibromopyrazin-2-amine (1 eq) was added, the reaction was warmed to rt and stirred for 3 h. The crude mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic phases were washed once each with H2O and brine, then dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 5-bromo-3-(2-methoxyethoxy)pyrazin-2-amine. LC/MS (m/z): 250.0 (MH+).

後処理

  1. temperaturethe reaction was warmed to rt
  2. customThe crude mixture was quenched with saturated aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed once each with H2O and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-852db8fd222a419190042c82bd509934
出典データセット
uspto-grants-2014_09
特許番号
US08822497B2

関連ノート

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