Acetic Anhydride → HCID 54566632, Verbindung

HRID 1645797

Reaktionsgleichung

Reaktionsgleichung von HRID 1645797
[CH3:1][C:2]([C:5]1[C:10]([O:11]COCCOC)=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[N:8]=[C:7]([CH2:22][CH:23]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)O)[N:6]=1)([CH3:4])[CH3:3].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[CH3:21][C:18]([C:9]1[C:10]([OH:11])=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[N:6]=[C:7]([CH:22]=[CH:23][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[N:8]=1)([CH3:19])[CH3:20]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 190071464,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-alpha-(3-pyridinyl)-2-pyrimidine-ethanol

Produkt 1

HCID 54566632HCID 54566632, VerbindungAusbeute 49,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
190 °C

Versuchsvorschrift

A mixture of 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-α-(3-pyridinyl)-2-pyrimidine-ethanol (350 mg), sodium acetate (10 g) and acetic anhydride (7 mL) in toluene (100 mL) is heated at reflux for 8 hours. The reaction mixture is cooled and the solvent is evaporated. Dichlorobenzene (30 mL) is added and the reaction mixture is heated at 190° C. for 30 minutes. The reaction mixture is cooled and partitioned between ethyl acetate and water. The aqueous layer is adjusted to pH 4 with 1 N HCl. The organic layer is collected and evaporated. Purification of the residue by flash chromatography (silica, 1:1 ethyl acetate/hexane) followed by recrystallization from hexane gives pure 4,6-bis(1,1-dimethylethyl)-2-[[2-(3 pyridinyl)]ethenyl]-5-pyrimidinol (130 mg, 40%); mp 150°-151° C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 8 hours
  3. temperatureThe reaction mixture is cooled
  4. customthe solvent is evaporated
  5. additionDichlorobenzene (30 mL) is added
  6. temperatureThe reaction mixture is cooled
  7. custompartitioned between ethyl acetate and water
  8. customThe organic layer is collected
  9. customevaporated
  10. customPurification of the residue by flash chromatography (silica, 1:1 ethyl acetate/hexane)
  11. customfollowed by recrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-80ecaebd6b5d4d8dbdd2a83fe26ae6e6
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05177079

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