| Identification | Back Directory | [Name]
6-CHLORO-7-METHYLPURINE | [CAS]
5440-17-5 | [Synonyms]
NSC 15192
6-CHLORO-7-METHYLPURINE
7-METHYL-6-CHLOROPURINE
6-Chloro-7-methyl-7H-purine | [Molecular Formula]
C6H5ClN4 | [MDL Number]
MFCD01943043 | [MOL File]
5440-17-5.mol | [Molecular Weight]
168.58 |
| Chemical Properties | Back Directory | [Appearance]
Light Green Solid | [Melting point ]
175-185°C | [Boiling point ]
321.7±45.0 °C(Predicted) | [density ]
1.59±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [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 |
| Hazard Information | Back Directory | [Chemical Properties]
Light Green Solid | [Uses]
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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