2,3-Diaminopyridine → Ethyl 8-amino-3-methylimidazo[1,2-a]pyridine-2-carboxylate

HRID 1166167Notes

Reaction equation

HRID 1166167 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:9]([O:11][C:12](=[O:18])[C:13](=O)[CH:14](Br)[CH3:15])[CH3:10].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[NH2:8][C:7]1[C:2]2[N:3]([C:14]([CH3:15])=[C:13]([C:12]([O:11][CH2:9][CH3:10])=[O:18])[N:1]=2)[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 99562,3-DiaminopyridineHCID 10340Sodium CarbonateHCID 11117285Ethyl 3-bromo-2-oxobutanoate

Product 1

HCID 22672637Ethyl 8-amino-3-methylimidazo[1,2-a]pyridine-2-carboxylateYield 34%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2,3-diaminopyridine (6.8 g, 62 mmol) and 3-bromo-2-oxo-butyric acid ethyl ester (13 g, 62 mmol) in 1,2-dimethoxyethane (150 ml) was refluxed for 2 h. Sodium carbonate (6.5 g, 62 mmol) was added and the mixture was refluxed for 2 h. The solids were isolated by filtration and washed with dichloromethane:methanol (10:1). The filtrate and washings were combined the solvents were removed under reduced pressure. The oily residue was washed with petroleum ether and was purified twice by column chromatography on silica gel using 1) dichloromethane:methanol (10:1) 2) ethyl acetate as eluent to give 4.6 g (34%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customThe solids were isolated by filtration
  3. washwashed with dichloromethane:methanol (10:1)
  4. customwere removed under reduced pressure
  5. washThe oily residue was washed with petroleum ether
  6. customwas purified twice by column chromatography on silica gel using 1) dichloromethane:methanol (10:1) 2) ethyl acetate as eluent

Sources & evidence

ORD record
ord-0a75be7eb90546bcb71f9161299fe8f6
Source dataset
uspto-grants-2003_09
Patent number
US06613775B1

Reaction notes

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