Dimethylformamide → HCID 57472502, compound

HRID 501456Notes

Reaction equation

HRID 501456 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]#[C:9][CH3:10].CN(C)C=O.[Cl:17][C:18]1[NH:28][C:21]2[CH:22]=[N:23][N:24]([CH3:27])[C:25](=[O:26])[C:20]=2[N:19]=1>C(OCC)(=O)C>[CH2:7]([N:19]1[C:20]2[C:25](=[O:26])[N:24]([CH3:27])[N:23]=[CH:22][C:21]=2[N:28]=[C:18]1[Cl:17])[C:8]#[C:9][CH3:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 136059619HCID 136059619, compound

Product 1

HCID 57472502HCID 57472502, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.166 g of potassium carbonate and 0.106 μl of 2-butynyl bromide were added to a 10 ml N,N-dimethylformamide solution of 0.184 g of 2-chloro-5-methyl-1,5-dihydroimidazo[4,5-d]pyridazin-4-one, and the mixture was stirred at room temperature for 18 hours. 50 ml of ethyl acetate was added to the solution, and the mixture was washed three times with 20 ml of water and then with 20 ml of a saturated sodium chloride solution. The organic liquid was dried over magnesium sulfate, and concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography. Thus, 0.175 g of 3-(2-butynyl)-2-chloro-5-methyl-3,5-dihydroimidazo[4,5-d]pyridazin-4-one was obtained from the fraction eluted with hexane-ethyl acetate (4:1), and 0.033 g of 1-(2-butynyl)-2-chloro-5-methyl-1,5-dihydroimidazo[4,5-d]pyridazin-4-one was obtained from the fraction eluted with hexane-ethyl acetate (2:3).

Workup

  1. washthe mixture was washed three times with 20 ml of water
  2. dry with materialThe organic liquid was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThen, the residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-456db7289c8b485e82028e3cf999d624
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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