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

HRID 78603

Reaction equation

HRID 78603 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

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) were stirred in MeCN (100 mL) at room temp for 16 hours. The resultant precipitate was filtered, washed with MeCN and dried under vacuum to give the desired product as a yellow solid (11.68 g, 92%). 1H NMR (400.0 MHz, DMSO) d 3.85 (3H, s), 7.55 (2H, br s), 8.42 (1H, s); MS (ES+) 233.78

Workup

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

Sources & evidence

ORD record
ord-75ab57f3f62b4c118c6e4ef8a74d2066
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Linked notes

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