Bromine → HCID 57764505, compound
Reaction equation
[C@@H:1]1([N:10]2[C:19]3[N:18]=[N:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].C([O-])(=O)C.[Na+].[Br:25]Br>>[NH2:15][C:14]1[C:13]2[N:12]=[C:11]([Br:25])[N:10]([C@@H:1]3[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]3[OH:3])[C:19]=2[N:18]=[N:17][N:16]=1Participants
4
Conditions
- Temperature
- 20 °C
Procedure
The 2-azaadenosine [for preparation see Patent WO 01/16149, 2001] (70 mg, 0.26 mmol) was added to a solution of sodium acetate 0.5M (1.4 mL). The solution was heated until the 2-azaadenosine was solubilized. A solution of bromine (100 μL of Br2 in 10 mL of water) (6.3 mL, 1.22 mmol) was added and the mixture was stirred at 20° C. for 3 days. A second portion of the bromine's solution (6.3 mL, 1.22 mmol) was added and the mixture was stirred at 20° C. for 3 hours. The reaction mixture was evaporated to dryness. The crude product was purified on silica gel reverse-phase (C18) using water/acetonitrile (9/1) as eluant to give the title compound as a yellow powder.
Workup
- stirringthe mixture was stirred at 20° C. for 3 hours
- customThe reaction mixture was evaporated to dryness
- customThe crude product was purified on silica gel reverse-phase (C18)
Sources & evidence
- ORD record
- ord-3d0d364796fc4052bc3b9dd5342619b2
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08742101B2
Reaction notes
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