Dimethylformamide → 2-{6-Azido-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol

HRID 2302

Reaktionsgleichung

Reaktionsgleichung von HRID 2302
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][CH2:9][CH2:10][OH:11])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.[N-:19]=[N+:20]=[N-:21].[Na+].CN(C)C=O>O>[N:19]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][CH2:9][CH2:10][OH:11])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)=[N+:20]=[N-:21]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 111189672-{6-Chloro-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol

Produkt 1

HCID 118077902-{6-Azido-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanolAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-{6-chloro-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (21.85 g), sodium azide (10.7 g) and dimethyformamide (260 ml) is heated with stirring at 75°-80° C. overnight. After cooling, the mixture is treated with water, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is crystallized from hexane to give 2-{6-azido-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol (19.6 g).

Aufarbeitung

  1. temperatureis heated
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer is washed
  5. customdried
  6. customevaporated
  7. customto remove the solvent
  8. customThe residue is crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-c78f869bf2a74b75ba8846f932a65794
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728706

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