6-Chloropurine riboside → HCID 15611205, Verbindung

HRID 845123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 845123
[C:1]1([C:7]2([CH2:13][NH2:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:15]1[N:20]=[C:19](Cl)[C:18]2[N:22]=[CH:23][N:24]([C@@H:25]3[O:29][C@H:28]([CH2:30][OH:31])[C@@H:27]([OH:32])[C@H:26]3[OH:33])[C:17]=2[N:16]=1>>[C:1]1([C:7]2([CH2:13][NH:14][C:19]3[C:18]4[N:22]=[CH:23][N:24]([C:17]=4[N:16]=[CH:15][N:20]=3)[C@@H:25]3[O:29][C@H:28]([CH2:30][OH:31])[C@@H:27]([OH:32])[C@H:26]3[OH:33])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

3

Edukt 2

HCID 930036-Chloropurine ribosideHCID 205110Cyclohexanemethylamine, 1-phenyl-

Produkt 1

HCID 15611205HCID 15611205, VerbindungAusbeute 42,4 %

Versuchsvorschrift

(1-Phenylcyclohexyl)methylamine (1.80 g, 8 mmol) as prepared below, and 6-chloropurine riboside (2.36 g, 8 mmol) are reacted as described in Example 1. The solvent is removed under reduced pressure, and the residue dissolved up in CHCl3 and washed with water and dried (MgSO4). The solvent is removed under reduced pressure and the residual white foam is purified on silica gel chromatography eluting with 10% MeOH in CH2Cl2 to give N6-((1-phenylcyclohexyl)methyl)adenosine (1.49 g, 42%) as a white glass m.p. 87°-9° C. Found: C, 62.22; H, 6.96; N, 15.70%. C23H29N5O4 calculated requires: C, 62.87; H, 6.61; N, 15.95%.

Aufarbeitung

  1. customare reacted
  2. customThe solvent is removed under reduced pressure
  3. dissolutionthe residue dissolved up in CHCl3
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent is removed under reduced pressure
  7. customthe residual white foam is purified on silica gel chromatography
  8. washeluting with 10% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-652a1ccacd814f8b86b6ed43fbedd285
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04755594

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