Water → 5-Bromo-3-methylpyrazin-2-amine

HRID 343364

Reaction equation

HRID 343364 reaction equation
[Br:1]Br.[NH2:3][C:4]1[C:9]([CH3:10])=[N:8][CH:7]=[CH:6][N:5]=1.N1C=CC=CC=1.O>C(Cl)(Cl)Cl>[NH2:3][C:4]1[C:9]([CH3:10])=[N:8][C:7]([Br:1])=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24408BromineHCID 3022842-Amino-3-methylpyrazine

Product 1

HCID 217851475-Bromo-3-methylpyrazin-2-amineYield 28%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of bromine (0.26 ml) in chloroform (40 ml) was added dropwise to a stirred solution of 2-amino-3-methylpyrazine (0.453 g) and pyridine (0.4 ml) in chloroform (100 ml) with shielding from sunlight, over a period of 1 hour. The reaction mixture was stirred for a further 30 minutes and then water (25 ml) was added. The organic layer was separated, dried (MgSO4) and evaporated to afford a brown oil. The oil was purified by chromatography on silica gel, eluting with dichloromethane, to give 2-amino-5-bromo-3-methylpyrazine as a white solid (0.312 g, 28%), m.p. 51°-52° C.; mass spectrum (+ve CI): 188 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto afford a brown oil
  5. customThe oil was purified by chromatography on silica gel
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-b0a34cb6b8cb4c5db4103c9247fa4714
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Linked notes

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