Reaktion #2075752

ord-49811c254f2e4cccb866f38f0232f9c7

Reaktionsgleichung

Nc1ncn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1
2′-deoxy-5-azacytidine
[BH4-].[Na+]
NaBH4
O
Water
→
NC1=NC(=O)N([C@H]2C[C@H](O)[C@@H](CO)O2)CN1
9
Ausbeute 86.9%
NC1=NC(=O)N([C@H]2C[C@H](O)[C@@H](CO)O2)CN1
1-(2-Deoxy-β-ribofuranosyl)-4-amino-1,2,5,6-tetrahydro-1,3,5-triazin-2-one
Ausbeute 86.9%

Edukte

Nc1ncn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1
2′-deoxy-5-azacytidine
[BH4-].[Na+]
NaBH4
O
Water

Reagenzien

Keine

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigegiving a clear solution that
  2. 2
    Sonstigewas directly used for RP HPLC purification
  3. 3
    SonstigeThe main fraction after evaporation

Vorschrift

Method A (Reduction of 2). To a suspension of 2′-deoxy-5-azacytidine (2) (0.045 g, 0.2 mmol) in 96% ethanol (2.9 mL) was added NaBH4 (40 mg, 1.06 mmol), and the mixture was stirred for 10 min at RT. Water (4 mL) was added to the mixture giving a clear solution that was directly used for RP HPLC purification using a gradient of MeCN in 0.1 M triethylammonium bicarbonate buffer. The main fraction after evaporation provided 0.04 g of 9 as a solid. MS ES+ 231 [M+H+].

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07642247B2uspto-grants-2010_01