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

HRID 2201573Notes

Reaction equation

HRID 2201573 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.C1C(=O)N([Br:19])C(=O)C1>CC#N>[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][C:5]([Br:19])=[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%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl 3-aminopyrazine-2-carboxylate (3.0 g, 19.6 mmol) and NBS (3.5 g, 23.5 mol) in MeCN (70 mL) was stirred at 70° C. for 5 h. Then the mixture was concentrated and extracted with EtOAc. The organic layer was washed with Na2SO3 (a.q.) and brine, dried over Na2SO4 and concentrated in vacuo. The crude product of methyl 3-amino-6-bromopyrazine-2-carboxylate (3.0 g, yield: 92%) was used for next step without further purification. 1H-NMR (CDCl3, 400 MHz) δ 8.18 (s, 1H), 6.54˜6.93 (m, 2H), 3.86 (s, 3H). MS (M+H)+: 232/234.

Workup

  1. concentrationThen the mixture was concentrated
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with Na2SO3 (a.q.) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-828290f45b244786a23fe10446582223
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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