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HCID 60018586, Verbindung → (2R,3R,4S,5R)-2-(2-(Aminomethyl)-6-{[2,2-bis(3-methylphenyl)ethyl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol

HRID 897124
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 897124
C([O:4][C@H:5]1[C@@H:9]([O:10]C(=O)C)[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([C:40]#[N:41])=[N:18][C:19]=3[NH:23][CH2:24][CH:25]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=2)[O:7][C@@H:6]1[CH2:42][O:43]C(=O)C)(=O)C>N.C(O)C.[Pd]>[NH2:41][CH2:40][C:17]1[N:16]=[C:15]2[C:20]([N:21]=[CH:22][N:14]2[C@H:8]2[C@H:9]([OH:10])[C@H:5]([OH:4])[C@@H:6]([CH2:42][OH:43])[O:7]2)=[C:19]([NH:23][CH2:24][CH:25]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=2)[N:18]=1
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Komponenten

5

Edukt 1

HCID 60018586HCID 60018586, Verbindung

Produkt 1

HCID 60018578(2R,3R,4S,5R)-2-(2-(Aminomethyl)-6-{[2,2-bis(3-methylphenyl)ethyl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiolAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 222AmmoniaLösungsmittel
HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

(2R,3R,4R,5R)-4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-(6-{[2,2-bis(3-methylphenyl)ethyl]amino}-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate (620 mg, 1 mmol) (Preparation 66) was dissolved in a saturated solution of 0.88 concentrated aqueous ammonia in ethanol (20 ml). The solution was then stirred under an atmosphere of hydrogen gas (414 kPa, 60 psi) at room temperature for 64 hours in the presence of 10% Palladium on carbon (120 mg). The reaction mixture was then filtered through Arbocel (Trade Mark) and the filtrate was evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:(90:10 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (80:20:2 by volume). The solvent was removed under reduced pressure to give the title compound (253 mg) as a foam.

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered through Arbocel (Trade Mark)
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane
  4. temperaturemethanol:(90:10 by volume) increasing in polarity to dichloromethane
  5. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4591768b7db3499db245bc763095f7f4
Quelldatensatz
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06921753B2

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