N-bromobutanimide → Ethyl 5-amino-6-bromopyrazine-2-carboxylate

HRID 596123Notes

Reaction equation

HRID 596123 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][CH:7]=1.C1C(=O)N([Br:20])C(=O)C1>C(#N)C.CCOC(C)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][C:7]=1[Br:20]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22271413Ethyl 5-Aminopyrazine-2-carboxylate

Product 1

HCID 118045269Ethyl 5-amino-6-bromopyrazine-2-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 5-aminopyrazine-2-carboxylate (880 mg, 5.26 mmol) in acetonitrile (20 mL) at RT was added NBS (984 mg, 5.53 mmol), the resultant solution was stirred at RT for 1 hour. The reaction mixture was diluted with EtOAc, washed with sat NaHCO3, brine and water, dried, filtered, and concentrated to afford the crude product, which was purified by ISCO 24 g silica gel column, 0 to 50% EtOAc in Heptane, 30 min). 1.01 g, 78% yield. LC-MS (m/z): 247.9 (MH+), 0.51 min.

Workup

  1. washwashed
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4d15e50efdc24c098cb0aeb7d6f0b9fa
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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