Phosphorus oxychloride → 4-chloro-5-nitropyrimidin-2-amine

HRID 260050Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 260050
[NH2:1][C:2]1[N:7]=[C:6](O)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:14])=O>>[NH2:1][C:2]1[N:7]=[C:6]([Cl:14])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178508524HCID 178508524, Verbindung

Produkt 1

HCID 3199954-chloro-5-nitropyrimidin-2-amine

Versuchsvorschrift

A suspension of 2-amino-4-hydroxy-5-nitropyrimidine (5.0 g, 32.1 mmol) in phosphorous oxychloride (100 mL) was refluxed overnight, and the excess phosphorous oxychloride was evaporated under reduced pressure. The residue was mixed with ice (100 g) in an ice-bath, and the mixture was neutralized with concentrated aqueous sodium carbonate solution. A yellow precipitate was collected by filtration and washed with water: yield, 1.39 g (25%); mp 191°-194° C. dec.; 1H NMR δ8.45 (br s, 2H, NH2, exchange with D2O), 9.03 (s, 1H, H-6); MS (EI) calcd. m/z for C4H3N4O235Cl 173.9944, found 173.9934; calcd. m/z for C4H3N4O237Cl 175.9915, found 175.9916.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. customthe excess phosphorous oxychloride was evaporated under reduced pressure
  3. additionThe residue was mixed with ice (100 g) in an ice-bath
  4. filtrationA yellow precipitate was collected by filtration
  5. washwashed with water
  6. customyield

Quellen und Nachweise

ORD-Eintrag
ord-f04d480b153c4f66a4694590139b5281
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05525606

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