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

HRID 1040372Notes

Reaction equation

HRID 1040372 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[N:11]=[CH:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[N:14][CH:15]=1>C(#N)C.CCOC(C)=O.O>[NH2:9][C:10]1[N:11]=[CH:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[N:14][C:15]=1[Br:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 14536427Methyl 5-aminopyrazine-2-carboxylate

Product 1

HCID 29983315Methyl 5-amino-6-bromopyrazine-2-carboxylateYield 78.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
20 °C

Procedure

Add 1.79 g (10.05 mmol) of N-bromosuccinimide to a solution of 1.4 g (9.14 mmol) of methyl 5-aminopyrazine-2-carboxylate in 10 mL of acetonitrile. Stir the reaction mixture for 2 h at 20° C. then distribute in 100 mL of EtOAc/water 1:1 mixture. Wash the organic phase with 2×50 mL of water, dry over Na2SO4 and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluting with a cyclohexane/EtOAc gradient from 0 to 50% of EtOAc. After concentration under reduced pressure, we obtain 1.66 g of methyl 5-amino-6-bromopyrazine-2-carboxylate in the form of yellow wax.

Workup

  1. washWash the organic phase with 2×50 mL of water
  2. dry with materialdry over Na2SO4
  3. concentrationconcentrate under reduced pressure
  4. customPurify the residue
  5. customobtained by silica gel column chromatography
  6. washeluting with a cyclohexane/EtOAc gradient from 0 to 50% of EtOAc
  7. concentrationAfter concentration under reduced pressure, we

Sources & evidence

ORD record
ord-c650f43a3d7c4499b5767d2488d3d667
Source dataset
uspto-grants-2013_10
Patent number
US08552201B2

Reaction notes

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