6-CHLORO-9-METHYLPURINE

6-CHLORO-9-METHYLPURINE is Pale Yellow Solid

To a solution of 6-chloro-9H-purine (3.00 g, 20.0 mmol) in anhydrous THF (100 mL)cooled to 0 8-Bromo-To a solution of 6-chloro-9H-purine (3.00 g, 20.0 mmol) in anhydrous THF (100 mL)cooled to 0 oC, 60% sodium hydride (1.2 g, 30.0 mmol) were added portionwise. After the reaction suspension was refluxed for 0.5 hour in the ice bath, MeI (2.82 g, 20.0 mmol) was added and the reaction mixture was stirred for 1 hour at room temperature. The mixture was diluted in 100 mL H2O and extracted with EtOAc (30 mL x 3). The combined organic layer was dried with anhydrous MgCl2 and the solvent was evaporated in vacuum. The crude solid was purified through a silica gel column, eluting with 20 % ether acetate/petroleum. White solid was obtained in a yield of 74.6% (2.50 g). ESI-MS m/z: 169.1 [M+H]+. 1H NMR (300 MHz, DMSO-d6): 3.72 (3H, s, CH3), 8.72 (1H, s, H-purine), 9.15 (1H, s, H-purine).To the compound 6-chloro-7H-purinele 59a (154.0 mg, 1.0 mmol) at room temperature, Sodium hydrogen (mineral oil dispersion 60%, 120.0 mg, 5.0 mmol) was mixed with N, N-dimethylacetamide (10 mL), and methyl iodide (426.0 mg, 3.0 mmol), reacted at room temperature for 24 hours. The reaction was quenched by the addition of 5 mL of water and extracted with dichloromethane (30 mL×3).The machine phase was washed with saturated brine (30 mL). Dry the organic phase with anhydrous sodium sulfate, remove the desiccant by filtration, and pass the residuePurification by flash column chromatography gave the title compound [0501] Procedure: To a stirred solution of 6-chloro-9H-purine (1 g, 6.469 mmol) in DMF (10 mL) was added Cs2CO3 (2.31g, 7.107 mmol) followed by methyl iodide (0.80 mL, 12.93 mmol). Reaction mixture was stirred for 3 h at room temperature. Progress of the reaction was monitored by TLC. Reaction mixture was diluted with water (20 mL), extracted with ethyl acetate (2 x 50mL). The combined organic layer was washed with brine (10mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The crude residue was purified by combiflash using methanol in dichloromethane to afford A mixture of 6-chloro-9H-purine (15.0 g, 97.4 mrnol), DM50 (200 mE) and K2C03 (20.2 g, 146 mmol) was treated dropwise with CH3I (20.7 g, 146 mmol) and stirred at RT overnight. Water (500 mL) was added and the resulting mixture was extracted with DCM (2 x500 mL). The combined organic extracts were washed with brine, dried with Na2SO4, Filtered and concentrated. The crude material was purified by column chromatography (1:1 petroleum ether/ethyl acetate) to give General procedure: To a solution of 9H-purines (1.5 mmol) and sodium hydride(0.12 g, 60%) in anhydrous DMF (3 mL) was added iodomethane (0.42 g, 3 mmol). The resulting mixture was stirred at room temperatureuntil the starting material disappeared on TLC. Then thereaction solution was poured into water (20 mL), and extractedthree times with EtOAc (15 mL x 3). The combined organic layerwas dried over anhydrous Na2SO4 and concentrated under reducedpressure to yield crude 9-methyl-9H-purine, which was used innext step without further purification

6-CHLORO-9-METHYLPURINE is a useful synthetic intermediate

Molecular Weight:168.58
XLogP3:1.3
Hydrogen Bond Acceptor Count:3
Exact Mass:168.0202739
Monoisotopic Mass:168.0202739
Topological Polar Surface Area:43.6
Heavy Atom Count:11
Complexity:154
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes