Potassium Carbonate → Methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-formylbenzoate

HRID 4904Notes

Reaction equation

HRID 4904 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]([C:9]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[O:8].[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>CN(C=O)C>[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([O:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:9]([CH:7]=[O:8])[C:10]=2[C:11]([O:13][CH3:14])=[O:12])[N:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 346008Methyl 2-formyl-6-hydroxybenzoateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidine

Product 1

HCID 14678388Methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-formylbenzoateYield 56.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

13.8 g of potassium carbonate and 50 ml of DMF were placed in a 200 ml eggplant type flask, and 11.1 g of methyl 2-formyl-6-hydroxybenzoate and 14.6 g of 4,6-dimethoxy-2-methanesulfonylpyrimidine were added thereto with stirring. The mixture was stirred at 80° C. for 1 hour, and the resultant liquor was poured into an ice water after cooling. An oily product thus precipitated was extracted with ethyl acetate, and was dried with magnesium sulfate anhydride. Ethyl acetate was distilled off under reduced pressure, and the residue thus obtained was purified by column chromatography to obtain 11.0 g of the aimed compound (melting point=91° to 93° C.) at a yield of 52%.

Workup

  1. stirringThe mixture was stirred at 80° C. for 1 hour
  2. temperatureafter cooling
  3. customAn oily product thus precipitated
  4. extractionwas extracted with ethyl acetate
  5. dry with materialwas dried with magnesium sulfate anhydride
  6. distillationEthyl acetate was distilled off under reduced pressure
  7. customthe residue thus obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-bef430985b434ffd803e950af8b3d2e0
Source dataset
uspto-grants-1993_09
Patent number
US05242895

Reaction notes

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