1-Bromo-2-butanone → 2-Ethyl-6-methylimidazo[1,2-b]pyridazine

HRID 1946457Notes

Reaction equation

HRID 1946457 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.Br[CH2:10][C:11](=O)[CH2:12][CH3:13]>C(O)CC>[CH2:12]([C:11]1[N:1]=[C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[N:4][N:3]2[CH:10]=1)[CH3:13]

Participants

4

Reactant 2

HCID 131561-Bromo-2-butanoneHCID 877126-Methylpyridazin-3-amine

Product 1

HCID 230281452-Ethyl-6-methylimidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

3-Amino-6-methylpyridazine (4.00 g, 27.5 mmol) and 1-bromo-2-butanone (90%, 7.38 g, 44.0 mmol) were heated in 1-propanol (40.0 ml) for 13 hours under reflux. The reaction solution was cooled to room temperature and concentrated under reduced pressure, and then the residues were dissolved in acetone (50.0 ml) and neutralized with 20% aqueous sodium hydroxide solution. The reaction solution was concentrated under reduced pressure, and then the residues were dissolved in chloroform, dried over anhydrous magnesium sulfate and concentrated. The residues were purified by silica gel column chromatography (isopropanol:hexane=1:2), to give the title compound as gray crystals. The yield was 2.33 g (39.4%).

Workup

  1. temperatureunder reflux
  2. concentrationconcentrated under reduced pressure
  3. dissolutionthe residues were dissolved in acetone (50.0 ml)
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. dissolutionthe residues were dissolved in chloroform
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residues were purified by silica gel column chromatography (isopropanol:hexane=1:2)

Sources & evidence

ORD record
ord-735bf20f6c69453ba687c01a32b28107
Source dataset
uspto-grants-2013_03
Patent number
US08399381B2

Reaction notes

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