Acetone → 2,4-Diiodopyrimidin-5-amine

HRID 1799576

Reaktionsgleichung

Reaktionsgleichung von HRID 1799576
CC(C)=O.Cl[C:6]1[N:11]=[C:10](Cl)[C:9]([N+:13]([O-])=O)=[CH:8][N:7]=1.O.O.[I-:18].[Na+].[IH:20]>[Fe].O>[I:18][C:6]1[N:11]=[C:10]([I:20])[C:9]([NH2:13])=[CH:8][N:7]=1

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 24841Hydrogen iodideHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 23685997Sodium iodide dihydrate

Produkt 1

HCID 582166432,4-Diiodopyrimidin-5-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A 4-necked roundbottom flask was charged with acetone (9.8 L), 2,4-dichloro-5-nitropyrimidine (670 g, 3.45 mol), and sodium iodide dihydrate (1929.6 g, 10.38 mol). Hydrogen iodide (67 ml, 40%) was then added dropwise. The resulting solution was allowed to react, with stirring, for three hours while the temperature was maintained at 20-30° C. Iron (978.6 g, 17.48 mol) was then added followed by the dropwise addition of water (300 ml). The resulting solution was allowed to react, with stirring, for an additional two hours while the temperature was maintained at reflux. The resulting slurry was filtered and the filtrate was concentrated under reduced pressure. The resulting aqueous solution was extracted four times with five liters of ethyl acetate. The combined organic layers were concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography eluting with 1:1 ethyl acetate/petroleum ether to afford the title compound.

Aufarbeitung

  1. customto react
  2. customto react
  3. stirringwith stirring, for an additional two hours while the temperature
  4. temperaturewas maintained
  5. temperatureat reflux
  6. filtrationThe resulting slurry was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. extractionThe resulting aqueous solution was extracted four times with five liters of ethyl acetate
  9. concentrationThe combined organic layers were concentrated under reduced pressure
  10. customThe resulting residue was purified via silica gel chromatography
  11. washeluting with 1:1 ethyl acetate/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-1020019b008d45e5965bb9f4053f5660
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344144B2

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