Sodium Azide → HCID 53813342, compound
Reaction equation
[OH:1][C@@H:2]([CH3:28])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]([CH2:25]Cl)=[N:12][C:11]=2[N:10]([CH3:27])[C:8]1=[O:9].[N-:29]=[N+:30]=[N-:31].[Na+]>CS(C)=O>[OH:1][C@@H:2]([CH3:28])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]([CH2:25][N:29]=[N+:30]=[N-:31])=[N:12][C:11]=2[N:10]([CH3:27])[C:8]1=[O:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A suspension of (S)-1-(5-hydroxyhexyl)-7-benzyl-8-chloromethyl-3-methylxanthine (2.0 g, 5.0 mmol) and sodium azide (1.62 g, 25 mmol) in methyl sulfoxide (15 ml) was stirred at 60° C. overnight. The reaction mixture was quenched by addition of water (30 ml) and extracted with ethyl acetate (3×25 ml). The combined extracts were washed with water (2×10 ml), with saturated aqueous sodium chloride solution (25 ml), dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with ethyl acetate to provide (S)-1-(5-hydroxyhexyl)-7-benzyl-8-azidomethyl-3-methylxanthine (1.7 g, 83% yield) as a colorless oil.
Workup
- customThe reaction mixture was quenched by addition of water (30 ml)
- extractionextracted with ethyl acetate (3×25 ml)
- washThe combined extracts were washed with water (2×10 ml), with saturated aqueous sodium chloride solution (25 ml)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by flash chromatography on silica gel eluting with ethyl acetate
Sources & evidence
- ORD record
- ord-1d2d701ba96e4f89a4ab1bbc2471e723
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06878715B1
Reaction notes
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