2H-Purine-2-thione, 6-amino-3,7-dihydro- → HCID 178420864, Verbindung

HRID 1597302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1597302
[NH:1]1[C:10](N)=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[N:4][C:2]1=S>C(O)CC.[Ni]>[N:1]1[CH:10]=[C:9]2[C:5](=[N:6][CH:7]=[N:8]2)[NH:4][CH:2]=1

Komponenten

4

Edukt 1

HCID 15020112H-Purine-2-thione, 6-amino-3,7-dihydro-

Produkt 1

HCID 178420864HCID 178420864, VerbindungAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

4.39 g (I1 mmoles) of thioisoguanine and 7.10 g (121 mmoles) of neutral Raney-nickel are refluxed in 50 ml of 1-propanol for 4.5 hours. The nickel was filtered off and the filtrate evaporated to dryness. The residue (3.79 g/93.8%) was dissolved in 20 ml of chloroform and 0.4 ml methanol and filtered through 24 g of silicagel in a column also with 2% methanol. The combined fractions were washed with 1N NaOH and the organic phase evaporated to dryness. The residue (2.69 g/66.6%) was dissolved in 30 ml of dichloromethane and 0.6 ml methanol and again filtered through 30 g of silicagel. A total of 1.86 g (46.0%) of 3H-purine was isolated, which was dissolved in 20 ml of methanol, treated with 5.4 ml of 1N methanolic HCl, and evaporated in vacuo to dryness. Crystallization and recrystallization from dichloromethane and ethyl acetate gave 1.75 g (39.4%) of 3H-purine hydrochloride with mp 170-85° C.

Aufarbeitung

  1. filtrationThe nickel was filtered off
  2. customthe filtrate evaporated to dryness
  3. dissolutionThe residue (3.79 g/93.8%) was dissolved in 20 ml of chloroform
  4. filtration0.4 ml methanol and filtered through 24 g of silicagel in a column also with 2% methanol
  5. washThe combined fractions were washed with 1N NaOH
  6. customthe organic phase evaporated to dryness
  7. dissolutionThe residue (2.69 g/66.6%) was dissolved in 30 ml of dichloromethane
  8. filtration0.6 ml methanol and again filtered through 30 g of silicagel

Quellen und Nachweise

ORD-Eintrag
ord-56ba332e63f44c7ab81cba775c8f9a2d
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06294541B1

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