2-Amino-6-Chloropyrazine → 3-Bromo-6-chloropyrazin-2-amine

HRID 1443936Notes

Reaction equation

HRID 1443936 reaction equation
[Br:1]NC(=O)CCC(N)=O.[Cl:10][C:11]1[N:16]=[C:15]([NH2:17])[CH:14]=[N:13][CH:12]=1.BrC1N=CC(N)=NC=1Cl>C(Cl)(Cl)Cl>[Br:1][C:14]1[C:15]([NH2:17])=[N:16][C:11]([Cl:10])=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 1184582-Amino-6-ChloropyrazineHCID 9834204N-BromosuccinamideHCID 181802075-Bromo-6-chloropyrazin-2-amine

Product 1

HCID 179559913-Bromo-6-chloropyrazin-2-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-bromosuccinamide (6.9 g) was added portionwise over 0.5 h to a stirred solution of 6-chloro-2-pyrazinamine (5.0 g) in chloroform (200 mL) heated under reflux. After the addition was complete the reaction mixture was allowed to cool, washed with water and evaporated to give a 3:1 mixture of 5-bromo-6-chloro-2-pyrazinamine and the subtitle compound which were separated by silica gel chromatography eluting with dichloromethane. Yield 2.0 g. Used directly.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. additionAfter the addition
  4. temperatureto cool
  5. washwashed with water
  6. customevaporated
  7. customto give
  8. customthe subtitle compound which were separated by silica gel chromatography
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-ba26584da5664429a6a77c885fde4624
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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