Hydrochloric Acid → 8-Chloro-3-octyl-3,7-dihydro-1H-purine-2,6-dione

HRID 2386651

Reaktionsgleichung

Reaktionsgleichung von HRID 2386651
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[NH:7][C:6](=[O:12])[NH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].I[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].N1CCOCC1.Cl>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[NH:7][C:6](=[O:12])[N:5]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:4]=2[N:3]=1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 10340Sodium CarbonateHCID 123801-IodooctaneHCID 261038-Chloroxanthine

Produkt 1

HCID 592995468-Chloro-3-octyl-3,7-dihydro-1H-purine-2,6-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

8-Chloro-3,7-dihydro-1H-purine-2,6-dione (100 mg, 0.44 mmol) was stirred with sodium carbonate (52 mg, 0.49 mmol) in dry DMF (3 ml) for 20 min., then 1-iodooctane (118 mg, 0.49 mmol) was added and the mixture was stirred under nitrogen at 40 C for 65 h. After cooling to room temperature, the mixture was thoroughly degassed by evacuating the vessel and refilling with nitrogen several times. Tetrakis(triphenylphosphine)palladium(0) (102 mg, 0.09 mmol) was added, the mixture degassed again and then morpholine (0.385 ml, 4.4 mmol) added and stirring continued for 6.5 h. 2M HCl and EtOAc were added, and the 2-phase system was filtered. The product was present predominantly in the filtered solid, which was recrystallised from THF-acetonitrile, followed by MeOH, with filtration, to afford the pure title compound.

Aufarbeitung

  1. customthe mixture was thoroughly degassed
  2. customby evacuating the vessel
  3. customthe mixture degassed again
  4. stirringstirring
  5. waitcontinued for 6.5 h
  6. filtrationthe 2-phase system was filtered
  7. customwas recrystallised from THF-acetonitrile
  8. filtrationfollowed by MeOH, with filtration

Quellen und Nachweise

ORD-Eintrag
ord-485829e54dfc466bafcf0e4400abf024
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268839B2

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