Potassium Carbonate → HCID 19436788, compound

HRID 1735005Notes

Reaction equation

HRID 1735005 reaction equation
[CH3:1][C:2]([C:5]1[CH:9]=[C:8]([OH:10])[N:7]([CH3:11])[N:6]=1)([CH3:4])[CH3:3].Cl[C:13]1[N:14]=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CS(C)=O>[CH3:4][C:2]([C:5]1[CH:9]=[C:8]([O:10][C:13]2[N:14]=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=2)[N:7]([CH3:11])[N:6]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 109756123-Chloro-5-methoxypyridazineHCID 178481821HCID 178481821, compound

Product 1

HCID 19436788HCID 19436788, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

3-(1,1-Dimethylethyl)-1-methyl-1H-pyrazol-5-ol (1.12 g, 0.0073 moles) which is a known compound, 3-chloro-5-methoxypyridazine (1.02 g, 0.0071 mole), potassium carbonate (1.87 g, 0.0136 mole), and CuBr (1.05 g, 0.0073 mole) were added to dry dimethyl-sulfoxide (12 mL). The mixture was stirred under N2 at 95° C. for 7 h. The mixture was then poured into saturated ammonium chloride and extracted 2×100 mL with ethyl acetate. The organic layer was dried (MgSO4), filtered through silica gel with ethyl acetate and evaporated in vacuo. The crude oil was flash chromatographed to give 3-[[3-(1,1-dimethylethyl)-1-methyl-1H-pyrazol-5-yl]oxy-5-methoxypyridazine (1.14 g, 62% yield) as an oil which solidified upon standing to a white solid.

Workup

  1. extractionextracted 2×100 mL with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered through silica gel with ethyl acetate
  4. customevaporated in vacuo
  5. customchromatographed

Sources & evidence

ORD record
ord-0a0e27fc88074e029fab1661c541ec38
Source dataset
uspto-grants-1996_07
Patent number
US05536701

Reaction notes

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