2-Butanone, 3-bromo- → Methyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate

HRID 427499Notes

Reaction equation

HRID 427499 reaction equation
[NH2:1][C:2]1[C:3]([NH2:12])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].Br[CH:14]([CH3:18])[C:15](=O)[CH3:16]>C(#N)C>[NH2:1][C:2]1[C:3]2[N:4]([C:14]([CH3:18])=[C:15]([CH3:16])[N:12]=2)[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=1

Participants

4

Reactant 2

HCID 131422-Butanone, 3-bromo-HCID 9920476Methyl 5,6-diaminopyridine-3-carboxylate

Product 1

HCID 9855934Methyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylateYield 59.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 5,6-diaminonicotinate (0.9 g, 5.4 mmol) and 3-bromo-2-butanon (0.9 g, 6.0 mmol) were added to acetonitril (30 ml) and refluxed for 24 h. Upon cooling some of the product was filtered off as hydrobromide salt. 20 ml of the filtrate was evaporated under reduced pressure and diethyl ether was added. More product was filtrated off as hydrobromide salt. The salt was dissolved in methylene chloride and washed with a bicarbonate solution. The organic layer was separated, dried over Na2SO4 and evaporated under reduced pressure to give 0.7 g (59%) of the desired compound.

Workup

  1. temperaturerefluxed for 24 h
  2. temperatureUpon cooling some of the product
  3. filtrationwas filtered off as hydrobromide salt
  4. custom20 ml of the filtrate was evaporated under reduced pressure and diethyl ether
  5. additionwas added
  6. filtrationMore product was filtrated off as hydrobromide salt
  7. dissolutionThe salt was dissolved in methylene chloride
  8. washwashed with a bicarbonate solution
  9. customThe organic layer was separated
  10. dry with materialdried over Na2SO4
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7a4693dde7f249f6af4f25b3e39efe2b
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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