2,6-Dichloropurine riboside Chemical Properties

Melting point:

>190°C (dec)

Boiling point:

542.2±60.0 °C(Predicted)

Density 

2.14±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly), Water

form 

Solid

pka

13.00±0.70(Predicted)

color 

White to Off-White

CAS DataBase Reference

13276-52-3(CAS DataBase Reference)

2,6-Dichloropurine riboside Usage And Synthesis

Chemical Properties

White to Off-White Solid

Uses

2,6-Dichloropurine-9-β-D-riboside is a useful reagent for the design of AB680 as potent and selective inhibitor of CD73.

Synthesis

Under nitrogen protection, 450 mL of fully acetyl-protected 2,6-dichloropurine riboside (0.1 mol) and anhydrous methanol were added to a three-necked flask equipped with a dropping funnel, stirred until the system was completely clarified, and cooled to -10°C. The reaction was carried out by TLC. Acetyl chloride (1.2 moles) was added slowly dropwise and after completion of the dropwise addition, the reaction was continued for 1.5 h. The progress of the reaction was monitored by TLC. After completion of the reaction, solid potassium carbonate was added to the system in batches until the pH reached 7-8 and the reaction mixture was filtered. The filtrate was concentrated to dryness, appropriate amount of water was added and extracted three times with 250 mL of ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated to dryness. Crystallization was carried out by adding 140 mL of isopropanol to give 27.3 g of 2,6-dichloropurine riboside as a white solid in 85% yield.

References

[1] Patent: CN105085595, 2017, B. Location in patent: Paragraph 0015; 0016; 0017; 0018

2,6-Dichloropurine riboside(13276-52-3)Related Product Information

• Carbon tetrachloride
• Dichloroethane
• Xylene
• Purine
• NAD+
• Guanosine
• 2,6-Dichloropurine
• 2,4-Dichlorobenzoic acid
• RIBAVIRINA
• 6-Chloropurine ribonucleoside
• 6-CHLOROPURINE-2'-DEOXYRIBOSIDE
• 2,6-Dichloropurine-2'-deoxyriboside
• 9-[2,3,5-TRI-O-ACETYL-BETA-D-RIBOFURANOSYL]-2,6-DICHLOROPURINE
• 6-CHLORO-9-(5-DEOXY-D-RIBOFURANOSYL)PURINE
• 2,6-Dichloropurine riboside