Acetic Anhydride → N2-acetyl-7-benzylguanine

Participants

Reaction Steps

Acetic anhydride (4.44 ml, 45.1 mmols) and 132.8 mg (0.598 mmols) of p-toluenesulfonic acid monohydrate were added to a solution of 4.37 g (13.9 mmols) of 7-benzylguanine dihydrochloride in 9 ml of acetic acid. The mixture was reacted at 105° C. for 3 hours, and then allowed to cool. Water (180 ml) was poured into the reaction solution, and 150 ml of a 5-% sodium hydrogencarbonate aqueous solution and 100 ml of a 1−N sodium hydroxide aqueous solution were added thereto to adjust the pH to 5.3. Crystals were filtered, washed with 50 ml of water, and then dried at 55° C. for 5 hours under reduced pressure to obtain 3.77 g (13.3 mmols) of N2-acetyl-7-benzylguanine as a white solid in a yield of 95.7%.

Provenance & Evidence