Potassium Carbonate → 5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)-1-pyrimidin-5-ylpyridazin-4(1H)-one

HRID 1528081Notes

Reaction equation

HRID 1528081 reaction equation
[CH3:1][O:2][C:3]1[C:4]([OH:20])=[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)[N:6]=[N:7][CH:8]=1.Br[C:22]1[CH:23]=[N:24][CH:25]=[N:26][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].COC1C2C(=C3C(=CC=2)C(OC)=CC=N3)N=CC=1.C(=O)([O-])O.[Na+]>CS(C)=O.[Cu]I>[CH3:1][O:2][C:3]1[C:4](=[O:20])[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)=[N:6][N:7]([C:22]2[CH:23]=[N:24][CH:25]=[N:26][CH:27]=2)[CH:8]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 783445-BromopyrimidineHCID 516892Sodium BicarbonateHCID 104622984,7-Dimethoxy-1,10-phenanthrolineHCID 178493808HCID 178493808, compound

Product 1

HCID 866865625-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)-1-pyrimidin-5-ylpyridazin-4(1H)-oneYield 8.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4-ol (100 mg), 5-bromopyrimidine (119 mg), potassium carbonate (155 mg), copper(I) iodide (14 mg) and 4,7-dimethoxy-1,10-phenanthroline (20 mg) in DMSO (2 mL) was stirred at 110° C. for 40 hr under an argon atmosphere. To the reaction mixture was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/methanol), and recrystallized from ethyl acetate/hexane to give the title compound (11 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (ethyl acetate/methanol)
  5. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-03ca3c2730494129871804e15e761e0c
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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