Water → Ethyl 2-(4,6-dimethoxypyrimidin-2-yloxy)benzoate

HRID 1885963

Reaktionsgleichung

Reaktionsgleichung von HRID 1885963
[H-].[Na+].[C:3]([O:12][CH2:13][CH3:14])(=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6].[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[N:20]=[C:19](S(C)(=O)=O)[N:18]=1.O>CN(C)C=O>[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[N:20]=[C:19]([O:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]([O:12][CH2:13][CH3:14])=[O:11])[N:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8365Ethyl SalicylateHCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidine

Produkt 1

HCID 14280503Ethyl 2-(4,6-dimethoxypyrimidin-2-yloxy)benzoateAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

After washing with petroleum ether, 3.9 grams (0.079 mole) of 60% sodium hydride in mineral oil was suspended in 15 mL of dimethylformamide. The suspension was cooled, and a solution of 10.8 grams (0.065 mole) of ethyl salicylate in 20 mL of dimethylformamide was added dropwise with stirring. Upon completion of addition, the reaction mixture was stirred at ambient temperature for one hour, and then 10.5 grams (0.048 mole) of 4,6-dimethoxy-2-methylsulfonylpyrimidine (prepared as in Example 1, Steps A-C) was added. Upon completion of addition, the reaction mixture was heated at 100° C. for 2.5 hours. The reaction mixture was cooled and poured into 250 mL of water. The mixture was extracted with ethyl acetate, and the extract was dried with magnesium sulfate. The mixture was filtered, and the filtrate was subjected to column chromatography on silica gel. Elution was accomplished using in succession 25% hexane in methylene chloride and 30% ethyl acetate in hexane. The appropriate fractions were combined and concentrated under reduced pressure to yield 12.5 grams of ethyl 2-(4,6-dimethoxypyrimidin-2-yloxy)benzoate. The nmr spectrum was consistent with the proposed structure.

Aufarbeitung

  1. temperatureThe suspension was cooled
  2. additionUpon completion of addition
  3. stirringthe reaction mixture was stirred at ambient temperature for one hour
  4. additionUpon completion of addition
  5. temperatureThe reaction mixture was cooled
  6. extractionThe mixture was extracted with ethyl acetate
  7. dry with materialthe extract was dried with magnesium sulfate
  8. filtrationThe mixture was filtered
  9. washElution
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-11317c5854a34236ba7754738bc7992d
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05149357

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