2-Amino-3,5-dibromopyrazine → 5-Bromo-3-ethoxypyrazin-2-amine

HRID 343369Notes

Reaction equation

HRID 343369 reaction equation
[NH2:1][C:2]1[C:7](Br)=[N:6][C:5]([Br:9])=[CH:4][N:3]=1.[O-:10][CH2:11][CH3:12].[Na+]>C(O)C>[NH2:1][C:2]1[C:7]([O:10][CH2:11][CH3:12])=[N:6][C:5]([Br:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6200042-Amino-3,5-dibromopyrazineHCID 2723922Sodium ethoxide

Product 1

HCID 126746115-Bromo-3-ethoxypyrazin-2-amineYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-amino-3,5-dibromopyrazine (obtained as described in Gazz. Chim. Ital., 1960, 90, 1807) (1.26 g) and sodium ethoxide (0.4 g) in ethanol (50 ml) was heated under reflux for 4 hours. Volatile material was removed by evaporation and the residue was partitioned between water (20 ml) and ethyl acetate (50 ml). The organic layer was separated and dried (MgSO4). Volatile material was removed by evaporation to give 2-amino-5-bromo-3-ethoxypyrazine (0.95 g); 1H NMR (d6 -DMSO): 1.4 (t, 3H), 4.3 (q, 2H), 6.4 (br s, 2H), 7.6 (s, 2H); mass spectrum (+ve CI): 218 (M+H)+.

Workup

  1. temperatureunder reflux for 4 hours
  2. customVolatile material was removed by evaporation
  3. customthe residue was partitioned between water (20 ml) and ethyl acetate (50 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. customVolatile material was removed by evaporation

Sources & evidence

ORD record
ord-fe396613a8f54efcbe5f8107b1e8dd44
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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