Ethanol → 5-Methoxy-2-(4-hydroxyphenyl)pyrimidine

HRID 485990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 485990
[H][H].Cl[C:4]1[C:9]([O:10][CH3:11])=[C:8](Cl)[N:7]=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([O:19]CC3C=CC=CC=3)=[CH:15][CH:14]=2)[N:5]=1.C(N(CC)CC)C.C(O)C>[Pd].O>[CH3:11][O:10][C:9]1[CH:8]=[N:7][C:6]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[N:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 8471TriethylamineHCID 190970644,6-Dichloro-5-methoxy-2-(4-benzyloxyphenyl)pyrimidineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 1357369415-Methoxy-2-(4-hydroxyphenyl)pyrimidineAusbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Hydrogen gas was blown into a mixture of 21 g of 4,6-dichloro-5-methoxy-2-(4-benzyloxyphenyl)pyrimidine, 18.1 g of triethylamine, 3.15 g of 10% palladium-on-carbon, 210 ml of ethanol, and 11 ml of water, followed by stirring at 40° C. for 6 hours. The catalyst was removed by filtration, and the filtrate was poured into 300 ml of water and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and distilled to remove ethyl acetate to afford 8.93 g (percent yield: 90.9%) of 5-methoxy-2-(4-hydroxyphenyl)pyrimidine.

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. additionthe filtrate was poured into 300 ml of water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationdistilled
  6. customto remove ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0bc80f25355f44b59294d2258f89aebc
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290477

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