Phosphorus oxychloride → 5-(3-Bromo-phenyl)-2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 1795450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1795450
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:22])[N:10]([CH3:21])[C:11](O)=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.O=P(Cl)(Cl)[Cl:25].C([O-])(O)=O.[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:22])[N:10]([CH3:21])[C:11]([Cl:25])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 1784816025-(3-bromo-phenyl)-2-hydroxy-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

Produkt 1

HCID 221851865-(3-Bromo-phenyl)-2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a 250 mL RBF, was added 5-(3-bromo-phenyl)-2-hydroxy-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (5.76 g, 16.1 mmol), 50 mL POCl3. The mixture was warmed up to 85° C. and stirred for 15 h under nitrogen. The mixture was cooled down to rt and vacuumed down all volatile composites. The black cake obtained was dissolved in dichloromethane, neutralized with sat. NaHCO3. After purified by flash chromatography, the 5-(3-Bromo-phenyl)-2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one was obtained in 4.72 g as white powder. MS (ES+): 376 (M+H)+; (ES−): 374 (M−H).

Aufarbeitung

  1. temperatureThe mixture was cooled down to rt
  2. customThe black cake obtained
  3. customAfter purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-271920d04eb14f02b0b5df2e8d91ff26
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026326B2

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