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

HRID 1107460Notes

Reaction equation

HRID 1107460 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 mnl) 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 a white solid, m.p. 51-52° C.; mass spectrum (+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-f083ef20d0b24f449a4cbe785a2bea5d
Source dataset
uspto-grants-2000_05
Patent number
US06060475

Reaction notes

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