Dimethylformamide dimethyl acetal → 3-Buten-2-one, 4-(dimethylamino)-3-imidazo[1,2-a]pyridin-6-yl-

HRID 414323Notes

Reaction equation

HRID 414323 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH2:10][C:11](=[O:13])[CH3:12])[CH:7]=[CH:6][C:5]=12.CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>CN(C)C=O>[CH3:16][N:17]([CH3:19])[CH:18]=[C:10]([C:8]1[CH:7]=[CH:6][C:5]2[N:4]([CH:3]=[CH:2][N:1]=2)[CH:9]=1)[C:11](=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 138523111-(Imidazo[1,2-a]pyridin-6-yl)propan-2-one

Product 1

HCID 541278533-Buten-2-one, 4-(dimethylamino)-3-imidazo[1,2-a]pyridin-6-yl-Yield 74.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 200 ml of N,N-dimethylformamide, 33.17 g of 1-(imidazo[1,2-a]pyridin-6-yl)-2-propanone was stirred at 80° C. for 1 hour, together with 45.4 g of N,N-dimethylformamide dimethyl acetal. After cooling, the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel chromatography (eluted with chloroform-methanol=97:3) to obtain 32.46 g (74.5%) of 4-dimethylamino-3-(imidazo[1,2-a]pyridin-6-yl)-3-buten-2-one.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe residue was purified by silica gel chromatography (eluted with chloroform-methanol=97:3)

Sources & evidence

ORD record
ord-3e792fef69084ec3b9ce30842ae40d29
Source dataset
uspto-grants-1988_12
Patent number
US04791202

Reaction notes

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