Bromine → Methyl 3-Amino-6-bromopyrazine-2-carboxylate

HRID 217769Notes

Reaction equation

HRID 217769 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].[Br:12]Br>CC(O)=O>[NH2:11][C:10]1[C:5]([C:3]([O:2][CH3:1])=[O:4])=[N:6][C:7]([Br:12])=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 72669Methyl 3-aminopyrazinecarboxylate

Product 1

HCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateYield 99.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

3-Aminopyrazine-2-carboxylic acid methyl ester (200 g, 1.3 mol, 3B Scientific Corporation) was dissolved in AcOH (1 L). The solution was warmed to 50° C. and Br2 (312 g, 1.9 mol) added dropwise. When the addition was completed, the mixture was stirred at 50° C. for additional 3 hours. The reaction mixture was poured slowly to ice-water (4 L). The precipitate was filtered, washed with water and dried under a reduced pressure to afford the subtitle compound (iii) as a red brown solid (300 g).

Workup

  1. additionWhen the addition
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried under a reduced pressure

Sources & evidence

ORD record
ord-b98dc2a0da1f43fdb404da166d6e5a7f
Source dataset
uspto-grants-2012_06
Patent number
US08198285B2

Reaction notes

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