Reaktion #1435755

ord-89e4b22e30c74c8091eb393e069be5a3

Reaktionsgleichung

O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)[nH]1
15
O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)[nH]1
1-(β-D-Arabinofuranosyl)uracil
II
iodine
O=[N+]([O-])O
HNO3
→
O=c1[nH]c(=O)n([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)cc1I
title compound 16
Ausbeute 62.0%
O=c1[nH]c(=O)n([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)cc1I
1-(β-D-Arabinofuranosyl)-5-iodouracil
Ausbeute 62.0%

Edukte

O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)[nH]1
15
O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)[nH]1
1-(β-D-Arabinofuranosyl)uracil
II
iodine
O=[N+]([O-])O
HNO3

Reagenzien

Keine

Lösungsmittel

ClC(Cl)Cl
CHCl3

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturwas heated
  2. 2
    Temperaturat reflux for 2 hours
  3. 3
    Temperaturcooled
  4. 4
    FiltrationThe crystalline solid was collected by filtration
  5. 5
    Waschenwashed with ether

Vorschrift

A mixture of 15 (1.2 g, 4.9 mmol), iodine (1.50 g, 5.9 mmol), CHCl3 (6 mL), and 1 N HNO3 (24 mL) was heated at reflux for 2 hours, and then cooled. The crystalline solid was collected by filtration and washed with ether to give the title compound 16 as a white solid (1.12 g, 62%). 1H NMR (DMSO-d6) δ 11.6 (s, 1H, NH), 8.10 (s, 1H, H-6), 5.95 (d, 1H, H-1′), 5.52 (br, 1H, OH), 5.40–5.10 (br, 1H, OH), 4.15–3.90 (m, 2H, H-2′, H-3′), 3.80–3.60 (m, 3H, H-4′, H-5′), 3.60–3.30 (m, 1H, OH).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07211570B2uspto-grants-2007_05