Dimethylformamide → Methyl 3-((6-amino-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)benzoate

Participants

Reaction Steps

A solution of Compound (3) (13.69 g) and potassium carbonate (8.75 g, 63.28 mmol) in DMF (“dimethylformamide”) (20 mL) was cooled to 0° C. Iodomethane (6.74 g, 47.46 mmol) was added to the solution and the mixture was allowed to warm to room temperature. After 30 minutes, the reaction was complete and was quenched with acetic acid. The quenched reaction mixture was extracted with ethyl acetate to give Compound (4) (7.36 g, 65% over two steps). 1H NMR (300 MHz, CDCl3) δ 3.43 (s, 3H), 3.77 (t, J=5.4, 10.2 Hz, 2H), 3.92 (s, 3H), 4.51 (t, J=4.8, 9.9 Hz, 2H), 5.32 (s, 2H), 7.45 (m, 3H), 7.65 (s, 1H), 8.03 (s, 1H). LCMS: m/z for C17H19N5O4++H observed 358.1 at 3.62 minutes of a 6 minute run, gradient 5-95% CH3CN in H2O. LCMS: m/z for C17H19N5O4++H observed 358.1 at 1.93 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O (C18 column).

Provenance & Evidence