Potassium Carbonate → 6-Chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehyde

HRID 1885959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885959
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([OH:10])[C:7]=1[CH:8]=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21](S(C)(=O)=O)[N:20]=1.[OH-].[Na+]>CN(C)C=O.O>[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([O:10][C:21]2[N:22]=[C:23]([O:25][CH3:26])[CH:24]=[C:19]([O:18][CH3:17])[N:20]=2)[CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 5283932-Chloro-6-hydroxybenzaldehydeHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidine

Produkt 1

HCID 156120076-Chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehydeAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Under a nitrogen atmosphere a solution of 2.0 grams (0.013 mole) of 6-chlorosalicylaldehyde in 10 mL of dimethylformamide was stirred, and 1.94 grams (0.0141 mole) of potassium carbonate was added. The reaction mixture was then stirred for 10 minutes, and a solution of 2.6 grams (0.013 mole) of 4,6-dimethoxy-2-methylsulfonylpyrimidine (prepared in Steps A-C) in 15 mL of dimethylformamide was added dropwise during a 10 minute period. Upon completion of addition, the reaction mixture was warmed to 60° C. where it was stirred for 18 hours. The reaction mixture was poured into 150 mL of water, cooled, and the pH was adjusted to 12 with aqueous 50% sodium hydroxide, with stirring. The mixture was stirred for 15 minutes, and the resultant solid was collected by filtration to yield 1.62 grams of 6-chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehyde. The nmr spectrum was consistent with the proposed structure. The reaction was repeated several times.

Aufarbeitung

  1. additionUpon completion of addition
  2. stirringwas stirred for 18 hours
  3. temperaturecooled
  4. stirringwith stirring
  5. stirringThe mixture was stirred for 15 minutes
  6. filtrationthe resultant solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e143988d045241db828b57601554fce5
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05149357

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