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

HRID 69945

반응식

HRID 69945 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-852db8fd222a419190042c82bd509934
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822497B2

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