2,6-DICHLORO-9-METHYL-9H-PURINE Chemical Properties

Melting point:

152-153℃

Boiling point:

307.2±52.0 °C(Predicted)

Density 

1.76

storage temp. 

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

pka

-0.90±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C6H4Cl2N4/c1-12-2-9-3-4(7)10-6(8)11-5(3)12/h2H,1H3

InChIKey

HWMJNDVUIMQFEW-UHFFFAOYSA-N

SMILES

N1C2C(=NC(Cl)=NC=2Cl)N(C)C=1

CAS DataBase Reference

2382-10-7

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933599590

2,6-DICHLORO-9-METHYL-9H-PURINE Usage And Synthesis

Uses

2,6-DICHLORO-9-METHYLPURINE acts as a reagent in the synthesis of highly selective inhibitors of PI3K-δ used in the treatment of inflammatory diseases such as leukocyte related illnesses.

Synthesis

Procedure for the synthesis of 2,6-dichloro-9-methyl-9H-purine (15b): potassium carbonate (K2CO3, 0.270 g, 1.95 mmol) was added to an anhydrous DMF (1.0 mL) solution of 2,6-dichloro-9H-purine (0.120 g, 0.635 mmol) at 0°C followed by the addition of iodomethane (0.20 mL, 3.21 mmol). The reaction mixture was stirred continuously at 0 °C for 5 hours. Upon completion of the reaction, the reaction was quenched with water and extracted with ethyl acetate (EtOAc). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate (MgSO4), concentrated and purified by silica gel (SiO2) column chromatography with an elution gradient from 100% hexane to 100% ethyl acetate (EtOAc) to afford the target product 15b (83.0 mg, 0.409 mmol, 64% yield) as a colorless solid. The product characterization data were as follows: IR (ATR, neat) 3067, 1554, 1360, 1333, 1223, 1147 cm-1; 1H NMR (CDCl3, 600 MHz) δ 8.09 (s, 1H), 3.89 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 153.3, 152.7, 151.3, 146.4, 130.4, 30.4.

References

[1] Patent: WO2014/189830, 2014, A1. Location in patent: Page/Page column 35
[2] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 12, p. 985 - 990
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 12, p. 3486 - 3490
[4] Patent: US2011/237607, 2011, A1. Location in patent: Page/Page column 6; 7
[5] Patent: WO2016/91916, 2016, A1. Location in patent: Page/Page column 66

2,6-DICHLORO-9-METHYL-9H-PURINE(2382-10-7)Related Product Information

• Purine