9-BENZYL-6-CHLORO-9H-PURINE Chemical Properties

Melting point:

86-87°C

storage temp. 

-20°C Freezer

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

Off-White

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

9-BENZYL-6-CHLORO-9H-PURINE Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

9-Benzyl-6-chloro-9H-purine is a useful intermediate in the synthesis of 1-substituted adenines.

Synthesis Reference(s)

The Journal of Organic Chemistry, 34, p. 1170, 1969 DOI: 10.1021/jo01256a103

Synthesis

GENERAL STEPS: Benzyl bromide (0.052 mL, 0.6 mmol) was added to a mixture of 6-chloropurine (0.056 g, 0.5 mmol) and sodium hydroxide (0.014 g, 0.6 mmol) in deionized water (2 mL). The reaction mixture was placed in a microwave reactor and irradiated at 0-400 W power (internal temperature maintained at 100 °C) for 10 min. Upon completion of the reaction, the mixture was concentrated under reduced pressure to remove the solvent and the residue was purified by column chromatography using ethyl acetate-cyclohexane (9:1, v/v) as eluent to give 9-benzyl-6-chloro-9H-purine in 82% yield.

References

[1] Nucleosides, Nucleotides and Nucleic Acids, 2016, vol. 35, # 2, p. 76 - 82
[2] European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 433 - 447
[3] Journal of Medicinal Chemistry, 1988, vol. 31, # 3, p. 606 - 612
[4] Tetrahedron Letters, 2014, vol. 55, # 18, p. 2929 - 2931
[5] Dalton Transactions, 2014, vol. 43, # 26, p. 9838 - 9842

9-BENZYL-6-CHLORO-9H-PURINE(1928-76-3)Related Product Information

• 7-BENZYL-6-CHLORO-7H-PURINE
• 6-chloro-9-(4-methoxybenzyl)-9H-purine
• 9-BENZYL-6-CHLORO-9H-PURINE
• 9-benzyl-2,6-dichloro-9H-purine
• 2,6-dichloro-9-(2-chlorobenzyl)-9H-purine
• 2,6-dichloro-9-(2-methoxybenzyl)-9H-purine
• 2,6-dichloro-9-(4-methylbenzyl)-9H-purine
• 2,6-dichloro-9-(3-methoxybenzyl)-9H-purine
• 6-chloro-9-(3-chlorobenzyl)-9H-purine
• 6-chloro-9-(4-fluorobenzyl)-9H-purine
• 9-(2-bromobenzyl)-2,6-dichloro-9H-purine
• 2,6-dichloro-9-(2-fluorobenzyl)-9H-purine
• 6-CHLORO-9-(1-PHENYL-ETHYL)-9H-PURINE
• 2,6-dichloro-9-(3-fluorobenzyl)-9H-purine
• 2,6-dichloro-9-(3-chlorobenzyl)-9H-purine
• [4-(6-CHLORO-PURIN-9-YLMETHYL)-PHENYL]-DIMETHYL-AMINE
• 6-chloro-9-(3-fluorobenzyl)-9H-purine
• 2,6-dichloro-9-(3-methylbenzyl)-9H-purine