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N-bromobutanimide → Methyl 3-Amino-6-bromopyrazine-2-carboxylate

HRID 78580
Notes
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Reaction equation

HRID 78580 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[Br:12]N1C(=O)CCC1=O>CC#N>[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][C:5]([Br:12])=[CH:6][N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 72669Methyl 3-aminopyrazinecarboxylate

Product 1

HCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateYield 92.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 3-aminopyrazine-2-carboxylate (8.35 g, 54.53 mmol) and N-bromo-succinimide (9.705 g, 54.53 mmol) was stirred in MeCN (100 mL) at room temp overnight. The resultant precipitate was filtered, washed with MeCN and dried to give the desired product as a yellow solid (11.68 g, 92% Yield)

Workup

  1. filtrationThe resultant precipitate was filtered
  2. washwashed with MeCN
  3. customdried

Sources & evidence

ORD record
ord-12edde3285584efcae9147bf026fb43f
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841308B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes