2-Butanone, 3-bromo- → 6-Methyl-8-phenylmethoxy-2,3-dimethylimidazo[1,2-b]pyridazine

HRID 358023

Reaction equation

HRID 358023 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([CH3:16])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Br[CH:18]([C:20](=O)[CH3:21])[CH3:19]>CO>[CH3:16][C:5]1[CH:6]=[C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:2]2[N:3]([C:18]([CH3:19])=[C:20]([CH3:21])[N:1]=2)[N:4]=1

Participants

4

Reactant 2

HCID 131422-Butanone, 3-bromo-HCID 155919113-Amino-6-methyl-4-phenylmethoxypyridazine

Product 1

HCID 155919126-Methyl-8-phenylmethoxy-2,3-dimethylimidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (0.01 mole) 3-amino-6-methyl-4-phenylmethoxypyridazine, [prepared following the methodology of Becket, et al. J. Pract. Chem., 311, 285(1969) and references cited therein], and (0.012 mole) 2-bromo-3-butanone in methanol is heated for 24 hours in a bath maintained at 100°. The mixture is cooled to room temperature and partitioned between aqueous sodium bicarbonate and methylene chloride. The layers are separated and the aqueous phase extracted with methylene chloride. The organic extracts are combined and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure to give 6-methyl-8-phenylmethoxy-2,3-dimethylimidazo[1,2-b]pyridazine.

Workup

  1. custom[prepared
  2. temperaturemaintained at 100°
  3. custompartitioned between aqueous sodium bicarbonate and methylene chloride
  4. customThe layers are separated
  5. extractionthe aqueous phase extracted with methylene chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-1717a85a15664a429084898fa46e5458
Source dataset
uspto-grants-1984_08
Patent number
US04464372

Linked notes

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