Ammonia → 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carbonitrile

HRID 2268409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268409
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([N:24]2[CH:32]=[N:31][C:30]3[C:25]2=[N:26][C:27]([C:48]#[N:49])=[N:28][C:29]=3[NH:33][CH2:34][CH:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:12][C@@H:11]1[CH2:50][O:51][CH3:52])(=O)C1C=CC=CC=1.N>CO>[OH:15][C@@H:14]1[C@H:10]([OH:9])[C@@H:11]([CH2:50][O:51][CH3:52])[O:12][C@H:13]1[N:24]1[CH:32]=[N:31][C:30]2[C:25]1=[N:26][C:27]([C:48]#[N:49])=[N:28][C:29]=2[NH:33][CH2:34][CH:35]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 59975289(2R,3R,4R,5R)-4-(benzoyloxy)-5-{2-cyano-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-2-(methoxymethyl)tetrahydro-3-furanyl benzoate

Produkt 1

HCID 599753059-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carbonitrileAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (2R,3R,4R,5R)-4-(benzoyloxy)-5-{2-cyano-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-2-(methoxymethyl)tetrahydro-3-furanyl benzoate (preparation 11) (6.75 g, 9.72 mmol) in methanol (300 ml) saturated with ammonia gas was stirred at room temperature for 72 hr. The solvent was removed under reduced pressure, the residue dissolved in dichloromethane and the solvent removed under reduced pressure (repeated). The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (98:2) gradually changing to dichloromethane:methanol (96:4). The residue was triturated with diethyl ether, filtered, washed with diethyl ether and dried to afford the title compound as a solid (2.20 g). MS: 487(MH+).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane
  3. customthe solvent removed under reduced pressure (repeated)
  4. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (98:2)
  5. customThe residue was triturated with diethyl ether
  6. filtrationfiltered
  7. washwashed with diethyl ether
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-dff8ace13ee14e76a0284c4be3f7b7da
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326359B1

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