Potassium Carbonate → HCID 54290489, compound

HRID 1491561Notes

Reaction equation

HRID 1491561 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24](S(C)(=O)=O)[N:23]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:2]([O:1][C:24]2[N:25]=[C:26]([O:28][CH3:29])[CH:27]=[C:22]([O:21][CH3:20])[N:23]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 54041789HCID 54041789, compound

Product 1

HCID 54290489HCID 54290489, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.2 g (4.7 mmol) of methyl 2-hydroxy-6-styrylbenzoate, 1.02 g (4.7 mmol) of 4,6-dimethoxy-2-methylsulphonyl-pyrimidine, 0.8 g (5.7 mmol) of potassium carbonate and 50 ml of acetonitrile is heated under reflux for 15 hours and then concentrated. The residue is shaken with methylene chloride/water, and the organic phase is dried with sodium sulphate and filtered. The filtrate is concentrated and the residue is purified by column chromatography (silica gel; hexane/ethyl acetate, 10:1). 1.0 g (54% of theory) of methyl 2-styryl-6-(4,6-di-methoxy-pyrimidin-2-yl-oxy)-benzoate is obtained as an amorphous product.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 15 hours
  3. concentrationconcentrated
  4. dry with materialthe organic phase is dried with sodium sulphate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated
  7. customthe residue is purified by column chromatography (silica gel; hexane/ethyl acetate, 10:1)

Sources & evidence

ORD record
ord-405fd24bfde64a98bcf8761f850dd62d
Source dataset
uspto-grants-1994_12
Patent number
US05371062

Reaction notes

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