6-CHLORO-7-METHYLPURINE Chemical Properties

Melting point:

175-185°C

Boiling point:

321.7±45.0 °C(Predicted)

Density 

1.59±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)

form 

Solid

pka

0.65±0.30(Predicted)

color 

Light Green to Grey-Blue

CAS DataBase Reference

5440-17-5

Safety Information

HS Code 

2933998090

6-CHLORO-7-METHYLPURINE Usage And Synthesis

Chemical Properties

Light Green Solid

Uses

6-CHLORO-7-METHYLPURINE is a useful synthetic intermediate.

Synthesis

To a 1L three-necked round-bottomed flask was added 6-chloro-9H-purine (15.4 g, 0.1 mol, 1 eq.) and tetrahydrofuran (155 mL) at 0 °C and protected by nitrogen in an inert atmosphere. Methylmagnesium chloride (MeMgCl, 36.6 mL, 1.0 M THF solution, 1.1 eq.) was added dropwise with stirring. The reaction mixture was continued to be stirred at 0 °C for 30 min. Subsequently, iodomethane (42.6 g, 3 eq.) was added slowly and dropwise with stirring. The resulting reaction solution was transferred to a 50 °C oil bath and the reaction was stirred for 5 hours. Upon completion of the reaction, the reaction was quenched by addition of 50 mL of aqueous ammonium chloride (NH4Cl) and extracted with dichloromethane (3 x 50 mL). The organic layers were combined and washed with brine (2 x 50 mL) and subsequently concentrated under vacuum. The crude product was recrystallized by dichloromethane/petroleum ether (1:10) to afford 6-chloro-7-methylpurine as a light green solid (7 g, 42% yield).

References

[1] Organic Letters, 2016, vol. 18, # 1, p. 16 - 19
[2] Patent: WO2018/96159, 2018, A1. Location in patent: Paragraph 0169-0172

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