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

HRID 1943834

Reaktionsgleichung

Reaktionsgleichung von HRID 1943834
[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-61bea09302c246549c77ace1e119f222
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394808B2

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