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

HRID 78575

Reaction equation

HRID 78575 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) 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); 1H NMR (400.0 MHz, DMSO) 3.85 (s, 3H), 7.55 (br s, 2H) and 8.42 (s, 1H) ppm; MS (ES+) 233

Workup

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

Sources & evidence

ORD record
ord-95349889551e442692e50934cd213786
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Linked notes

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