Hydrogen Peroxide → 8-(trifluoromethyl)-7H-purine-2,6-diamine

HRID 1363453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363453
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH2:11])[N:3]=1.[F:12][C:13](I)([F:15])[F:14].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7]([C:13]([F:15])([F:14])[F:12])=[N:8]2)=[C:4]([NH2:11])[N:3]=1

Komponenten

6

Edukt 3

HCID 784Hydrogen PeroxideHCID 16843TrifluoroiodomethaneHCID 309762,6-Diaminopurine

Produkt 1

HCID 36354078-(trifluoromethyl)-7H-purine-2,6-diamineAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24393Ferrous SulfateKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

0.15 g (1.0 mmol) of 2,6-diaminopurine was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 4.0 ml of dimethyl sulfoxide, 1.0 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.3 ml of a 1.0 mol/l aqueous solution of iron (II) sulfate and 0.2 ml of a 30% hydrogen peroxide aqueous solution. The mixture was stirred at 40 to 50° C. for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 2,6-diamino-8-trifluoromethylpurine (19F-NMR yield: 45%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 2,6-Diamino-8-trifluoromethylpurine was obtained as a white solid (0.050 g, yield: 23%) by column chromatography.

Aufarbeitung

  1. customplaced in a 50 ml two-neck flask
  2. customequipped with a magnetic rotor
  3. additionThe following materials were added
  4. temperaturethe resulting solution was cooled to room temperature

Quellen und Nachweise

ORD-Eintrag
ord-23b434d1bb4141a38e18faddf570d8f1
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884202B2

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