4-Methylpyrazole → HCID 57743113, compound

HRID 910134Notes

Reaction equation

HRID 910134 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[N:6][NH:7][CH:8]=1.Cl[C:10]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[C:14]([CH3:23])[N:13]=[N:12][C:11]=1[CH3:24].C(OCC)(=O)C>CN(C=O)C>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]2[C:10]([N:6]3[CH:5]=[C:4]([CH3:3])[CH:8]=[N:7]3)=[C:11]([CH3:24])[N:12]=[N:13][C:14]=2[CH3:23])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 34064-MethylpyrazoleHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 57743122HCID 57743122, compound

Product 1

HCID 57743113HCID 57743113, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

87 mg of sodium hydride (55% oil dispersion) was added to 3 ml of DMF, and to this was added a solution of 0.16 g of 4-methylpyrazole in 3 ml of DMF, and the mixture was stirred for 0.5 hours at room temperature. To the resultant mixture was added 0.25 g of 4-chloro-5-(4-chlorophenyl)-3,6-dimethylpyridazine, and the mixture was stirred for 3 hours on an oil bath of 80° C. To the reaction mixture was added ethyl acetate, and washed with brine four times. The organic layer was dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure. 0.40 g of the resultant residue was subjected to silica gel column chromatography, to obtain 0.21 g of 5-(4-chlorophenyl)-3,6-dimethyl-4-(4-methyl-1-pyrazolyl)pyridazine (hereinafter, described as compound (5) of the present invention.).

Workup

  1. stirringthe mixture was stirred for 3 hours on an oil bath of 80° C
  2. washwashed with brine four times
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dae0d567845c4db0be1ea8213613537d
Source dataset
uspto-grants-2011_09
Patent number
US08022073B2

Reaction notes

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