Phosphorus oxychloride → 2-Chloro-3-methyl-6-pyridin-4-yl-5-m-tolyl-3H-pyrimidin-4-one

HRID 897395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 897395
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)=[C:5]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[NH:4][C:3]1=O.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:3]1[N:2]([CH3:1])[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)=[C:5]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[N:4]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 223465713-methyl-5-(3-methylphenyl)-6-(4-pyridyl)-2,4(1H,3H)-pyrimidindione

Produkt 1

HCID 161156882-Chloro-3-methyl-6-pyridin-4-yl-5-m-tolyl-3H-pyrimidin-4-one

Versuchsvorschrift

A mixture of 3-methyl-5-(3-methylphenyl)-6-(4-pyridyl)-(1H,3H)-pyrimidin-2,4-dione (12.5 g, 0.043 mol) and phosphorus oxychloride (65 ml) was refluxed for 16 h. The excess of phosphorus oxychloride was evaporated followed by co-distillation with toluene. The remainder was carefully partitioned between dichloromethane and aqueous sodium hydrogencarbonate. The organic solution was washed with water, dried and evaporated to leave the title compound; MS (m/z): 312 (M+H)+; C17H14ClN3O requir. 311.8.

Aufarbeitung

  1. temperaturewas refluxed for 16 h
  2. customThe excess of phosphorus oxychloride was evaporated
  3. customThe remainder was carefully partitioned between dichloromethane and aqueous sodium hydrogencarbonate
  4. washThe organic solution was washed with water
  5. customdried
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1059941cf10f477584ed5ef9d9eb8408
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921762B2

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