Acetonitrile → 6-Isopropyl-2-methylimidazo[1,2-b]pyridazine

HRID 1160767Notes

Reaction equation

HRID 1160767 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:6][CH:7]=1.Br[CH2:12][C:13](=O)[CH3:14].C(#N)C.[OH-].[Na+]>O>[CH:8]([C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:12]=[C:13]([CH3:14])[N:1]=2)[N:4]=1)([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11715BromoacetoneHCID 14798Sodium HydroxideHCID 230281096-Isopropylpyridazin-3-amine

Product 1

HCID 230281396-Isopropyl-2-methylimidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Amino-6-isopropylpyridazine (0.41 g, 2.99 mmol) and bromoacetone (0.53 g, 3.10 mmol) were mixed with acetonitrile (5.0 ml) and heated for 6 hours under reflux. After the reaction was completed, water (20.0 ml) was poured into the reaction solution and adjusted to pH 9 with 20% aqueous sodium hydroxide solution. The reaction solution was extracted twice with ethyl acetate, and the extracts were combined, dried over anhydrous sodium sulfate and concentrated. The residues were purified by silica gel column chromatography (ethyl acetate:chloroform=1:1) to give the title compound as brown oil. The yield was 0.30 g (57.2%).

Workup

  1. temperatureheated for 6 hours
  2. temperatureunder reflux
  3. extractionThe reaction solution was extracted twice with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residues were purified by silica gel column chromatography (ethyl acetate:chloroform=1:1)

Sources & evidence

ORD record
ord-eb7e0794ddcd429a983eda48e6967952
Source dataset
uspto-grants-2010_10
Patent number
US07816526B2

Reaction notes

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