N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide Chemical Properties

Melting point:

174 °C

Density 

1.50

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

form 

Solid

pka

8.74±0.20(Predicted)

color 

White to Pale Beige

CAS DataBase Reference

86357-14-4(CAS DataBase Reference)

Safety Information

HS Code 

2933.99.9701

N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide Usage And Synthesis

Chemical Properties

Light Brown Solid

Uses

Ganciclovir derivative.

Synthesis

The general procedure for the synthesis of 2-((2-acetylamino-6-oxo-1H-purin-9(6H)-yl)methoxy)propane-1,3-diyl diacetate from 2-(acetyloxymethoxy)-1,3-propanediol diacetate and N-(9-acetyloxy-6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide is as follows: first, 50.0 g ( 0.21 mol, 1.0 eq.) of 20.0-diacetylguanine, 104.2 g (0.42 mol, 2.0 eq.) of 1,3-diacetoxy-2-(acetyloxymethoxy)propane and 3.0 g (0.021 mol, 0.1 eq.) of boron trifluoride ether compounds were mixed with 200 g of N,N-dimethylformamide in a microwave reactor. The reaction mixture was heated to 100 °C and maintained at this temperature for 10 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the mixture was cooled to room temperature. Subsequently, 450 g of ethyl acetate was added to the mixture and refluxed for 1 hour, after which the temperature was reduced to 0-5 °C and maintained for 1 hour. After filtration and drying process, 68.3 g of triacetyl ganciclovir compound (2) was obtained in 85.3% yield and 95.6% purity, while 3.1% of compound (3) was obtained.

References

[1] Patent: CN108467396, 2018, A. Location in patent: Paragraph 0030; 0031; 0036; 0037; 0040; 0041; 0044; 0045

N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide(86357-14-4)Related Product Information

• 2-Ethoxyphenol
• acetic acid, triethoxy-, ethyl ester
• Ethoxyquin
• Dihydromyrcenol
• Ganciclovir
• DIETHOXYMETHANE
• Methyl acrylate
• Methyl salicylate
• 4-Ethoxyphenol
• Methanol
• Kresoxim-methyl
• Valganciclovir
• Methylparaben
• Tribenuron methyl
• Basic Violet 1
• Ganciclovir sodium
• Methyl
• 9-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine