N-Benzyl-2-chloro-9H-purin-6-amine Chemical Properties

Melting point:

239-241℃

Boiling point:

407.7±55.0 °C(Predicted)

Density 

1.49

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chloroform, DMSO, Ethyl Acetate

form 

Solid

pka

7.11±0.20(Predicted)

color 

White

N-Benzyl-2-chloro-9H-purin-6-amine Usage And Synthesis

Uses

2-Chloro-N-(phenylmethyl)-1H-purin-6-amine is an intermediate in the synthesis of Olomoucine (O567000), a purine derivative which inhibits cyclin-dependent kinases and induces G1 arrest.

Synthesis

Synthesis of N-benzyl-2-chloro-9H-purin-6-amine (4): 2,6-dichloropurine (110 mg, 0.52 mmol) was suspended in n-butanol (3 mL) and benzylamine (57 mg, 0.52 mmol) and triethylamine (72 mg, 0.79 mmol) were added sequentially. The reaction mixture was heated at 60 °C with stirring for 15 min. Upon completion of the reaction, the precipitate was collected by filtration and washed sequentially with water (20 mL) and methanol (10 mL), followed by drying in air overnight to give off-white solid product 4 (130 mg, 95% yield). The product was characterized as follows: melting point 262 °C; EI/MS m/z (relative abundance): 259 (19, M+), 260 (14), 261 (17%), 106 (100), 91 (77); 1H NMR (400 MHz, DMSO-d6) δ 8.15 (s, 1H), 7.25-7.34 (m, 5H), 4.66 (d J = 6 Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ 155.0 (s), 153.1 (s), 150.7 (s), 140.2 (d, 1JC-H = 200 Hz), 139.6 (s), 128.5 (d, 2JC-H = 158 Hz), 127.5 (d, 3JC-H = 157 Hz), 127.0 (d, 4JC-H = 158 Hz), 118.1 (s), 43.4 (t, 2JC-H = 139 Hz).

References

[1] Organic Process Research and Development, 2009, vol. 13, # 3, p. 641 - 644
[2] Synthetic Communications, 2010, vol. 40, # 12, p. 1856 - 1866
[3] Patent: WO2012/51296, 2012, A2. Location in patent: Page/Page column 40
[4] Archiv der Pharmazie, 1999, vol. 332, # 6, p. 187 - 190
[5] Nucleosides, Nucleotides and Nucleic Acids, 2011, vol. 30, # 7-8, p. 503 - 511

N-Benzyl-2-chloro-9H-purin-6-amine(39639-47-9)Related Product Information

• 1-[2-CHLORO-6-[[(3-IODOPHENYL)METHYL]AMINO]-9H-PURIN-9-YL]-1-DEOXY-N-METHYL-BETA-D-RIBOFURANURONAMIDE
• 6-benzylaminopurine hydrochloride
• N-BENZYL-N-(2-CHLOROPYRIMIDIN-4-YL)AMINE
• 2-CHLORO-N-METHYL-9H-PURIN-6-AMINE
• N-BENZYL-2-CHLORO-9-ISOPROPYL-9H-PURIN-6-AMINE
• N-Benzyl-2-chloro-9H-purin-6-amine