Bromine → Methyl 3-((6-amino-8-bromo-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)benzoate

Participants

Reaction Steps

A solution of Compound (4) (4.09 g, 11.45 mmol) and sodium acetate (14.26 g, 171.84 mmol) in acetic acid (50 mL) was cooled to 0° C. in an ice bath. Bromine (23.8 g, 148.93 mmol) was added dropwise by syringe. The reaction mixture was allowed to warm to room temperature and stirred overnight (16 hr), and subsequently quenched with saturated sodium sulfite solution. The quenched reaction mixture was extracted with dichloromethane (3×50 mL), dried over sodium sulfate and solvent evaporated to give Compound (5) as a yellow solid (3.35 g, 67% yield). 1H NMR (300 MHz, CDCl3) δ 3.44 (s, 3H), 3.77 (t, J=5.1, 9.9 Hz, 2H), 3.92 (s, 3H), 4.52 (t, J=4.8, 9.9 Hz, 2H), 5.35 (s, 2H), 7.41 (t, J=7.5, 13.5, Hz, 1H), 7.49 (d, J=7.8 Hz, 1H), 7.98 (d, J=7.8 Hz, 1H), 8.09 (s, 1H). LCMS: m/z for C17H18BrN5O4++H observed 437.0 and 438.0 at 3.62 minutes of a 6 minute run, gradient 5-95% CH3CN in H2O (C18 column).

Provenance & Evidence