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) |
|---|---|
| Pages (from-to) | 1709-1713 |
| Number of pages | 5 |
| Journal | Chinese Journal of Organic Chemistry |
| Volume | 26 |
| Issue number | 12 |
| State | Published - Dec 2006 |
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Keywords
- 2-amino-6-fluoro-9-(4-hydroxy-3-hydroxymethylbutyl)purine
- Antiviral agent
- Fluorination reaction
- Synthesis
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Synthesis of 2-Amino-6-fluoro-9-(4-hydroxy-3-hydroxymethylbutyl)purine. / Cai, Han Cheng; Yin, Duan Zhi; Zhang, Lan; Wang, Yong Xian.
In: Chinese Journal of Organic Chemistry, Vol. 26, No. 12, 12.2006, p. 1709-1713.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of 2-Amino-6-fluoro-9-(4-hydroxy-3-hydroxymethylbutyl)purine
AU - Cai, Han Cheng
AU - Yin, Duan Zhi
AU - Zhang, Lan
AU - Wang, Yong Xian
PY - 2006/12
Y1 - 2006/12
N2 - 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.
AB - 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.
KW - 2-amino-6-fluoro-9-(4-hydroxy-3-hydroxymethylbutyl)purine
KW - Antiviral agent
KW - Fluorination reaction
KW - Synthesis
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UR - http://www.scopus.com/inward/citedby.url?scp=33846550780&partnerID=8YFLogxK
M3 - Article
VL - 26
SP - 1709
EP - 1713
JO - Chinese Journal of Organic Chemistry
JF - Chinese Journal of Organic Chemistry
SN - 0253-2786
IS - 12
ER -