Potassium Carbonate → Methyl 3-((6-amino-2-chloro-9H-purin-9-yl)methyl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-6-aminopurine (1) (10 g, 58.97 mmol) and potassium carbonate (10 g, 744 mmol) in DMF (100 mL) was added methyl 3-(bromomethyl)benzoate (13.5 g, 58.93 mmol). The reaction mixture was heated to 60° C. for 90 minutes at which time the reaction was quenched by adding water. The quenched reaction mixture was extracted with ethyl acetate (3×50 mL) giving 16 g (86%) of Compound (2) as a white solid, which was used in the next step without further purification. 1H NMR (300 MHz, DMSO) δ 3.83 (s, 3H), 5.42 (s, 2H), 7.53 (m, 2H), 7.89 (m, 2H), 8.29 (s, 1H). LCMS: m/z for C14H12ClN5O2++H observed 318.1 at 1.99 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O (C18 column).

Provenance & Evidence