Acetyl chloride → 2-Chloro-6-(2-propylimidazol-1-yl)purine

Participants

Reaction Conditions

Reaction Steps

9-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-2-chloro-6-(2-propylimidazol-1-yl)purine (4.99 g, 9.6 mmol) was dissolved in HOAc (400 mL). To the solution was added AcCl (4.0 mL, 4.42 g, 56.3 mmol), and the mixture was stirred at 65° C. for 1.5 h in a sealed flask (reaction almost complete, TLC). Volatiles were evaporated in vacuo, and the residue was washed (CH2Cl2), and dissolved in 0.1 N NaOH/H2O. Precipitation with CO2 gave 2-chloro-6-(2-propylimidazol-1-yl)purine (2.20 g, 88%). Recrystallization (MeOH) gave the pure material (1.93 g, 77%).

Provenance & Evidence