Adenine → 9-Methyladenine

Participants

Reaction Steps

Adenine (2.0 g, 14.8 mmol), tetrahydrofuran (100 mL) and tetrabutyl-ammonium-fluoride solution in 1.0 M tetrahydrofuran (37 mL, 37 mmol) were added in 300 mL mad apple-type flask with a magnetic stirrer. Methyl-iodide (2.72 mL) added drop wise to the solution in 10 minutes during stirring and allowed to stir for 2.5 hr. The reaction solution was evaporated under reduced pressure. The residues were dissolved in methanol and filtered. The filtrate was added ethanol-water mixture. The object was recrystallized in ethanol-water mixture to give white solids (1.0 g, yield, 45%). 1H NMR (400 MHz, DMSO-d6): δ 3.70 (s, 3H), 7.15 (br, 2H), 8.07 (s, 1H), 8.13 (s, 1H), 13C NMR (100 MHz, DMSO-d6): δ 29.3, 118.6, 141.3, 149.8, 152.4, 155.9; MS (ESI+)calcd for C6H7N5+(M+H+) 150.0774, found 150.0914.

Provenance & Evidence