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

HRID 69945

Reaction equation

HRID 69945 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-852db8fd222a419190042c82bd509934
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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