Bromine → 2-Amino-3-bromo-5-methylpyrazine

HRID 1378344Notes

Reaction equation

HRID 1378344 reaction equation
[Br:1]Br.[NH2:3][C:4]1[CH:9]=[N:8][C:7]([CH3:10])=[CH:6][N:5]=1>C(Cl)(Cl)Cl>[NH2:3][C:4]1[C:9]([Br:1])=[N:8][C:7]([CH3:10])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 3132155-Methylpyrazin-2-amine

Product 1

HCID 98990432-Amino-3-bromo-5-methylpyrazine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of bromine (0.11 ml) in chloroform (20 ml) was added dropwise over 20 minutes to a solution of 2-amino-5-methylpyrazine (0.218 g) in chloroform (30 ml) which was protected from light. The reaction mixture was stirred for 90 minutes after addition was complete and was then washed with water (50 ml). The organic phase was dried (MgSO4) and volatile material was removed by evaporation to give a yellow oil. The oil was purified by elution with dichloromethane through a silica gel Mega Bond Elut column to give 2-amino-3-bromo-5-methylpyrazine (0.286 g) as white solid, m.p. 51°-52° C.; mass spectrum (positive chemical ionisation (+ve CI)): 188 (M+H)+.

Workup

  1. additionafter addition
  2. washwas then washed with water (50 ml)
  3. dry with materialThe organic phase was dried (MgSO4) and volatile material
  4. customwas removed by evaporation
  5. customto give a yellow oil
  6. customThe oil was purified by elution with dichloromethane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-3ddaff25c86a4baca01be39fb54d7501
Source dataset
uspto-grants-1997_09
Patent number
US05668137

Reaction notes

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