Abstract
The fluorinated nucleoside analogue 2-amino-6-fluoro-9-(4-hydroxy-3- hydroxymethylbutyl)purine (1) is a potential antiviral agent and 18F-radiopharmaceutical reference compound. Its synthesis was described. 2-Amino-6-chloro-9-(4-acetoxy-3-acetoxymethylbutyl)purine (2) was hydrolyzed to 2-amino-6-chloro-9-(4-hydroxy-3-hydroxymethylbutyl)purine (3) by using potassium carbonate in a mixed solution of water and methanol at 0 °C, then was converted to the corresponding trimethylammonium chloride (4) by treatment with trimethylamine (TMA) in ethanolic solution in a mild condition. Compound 4 was reacted with anhydrous KF in DMF to produce 2-amino-6-fluoro-9- (4-hydroxy-3-hydroxymethylbutyl)purine (1) in 87.3% yield. The structures of the products were characterized by UV-vis, IR, NMR and MS spectra. Some factors affecting the yield of fluorination reaction were investigated.
Original language | English (US) |
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Pages (from-to) | 1709-1713 |
Number of pages | 5 |
Journal | Chinese Journal of Organic Chemistry |
Volume | 26 |
Issue number | 12 |
State | Published - Dec 1 2006 |
Keywords
- 2-amino-6-fluoro-9-(4-hydroxy-3-hydroxymethylbutyl)purine
- Antiviral agent
- Fluorination reaction
- Synthesis
ASJC Scopus subject areas
- Organic Chemistry