Diisobutylaluminum hydride → (3-((6-amino-8-bromo-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of Compound (5) (3.35 g, 7.67 mmol) in THF (“tetrahydrofuran”) (20 mL) cooled to 0° C. was added a 1 M solution of DIBAL-H (34.5 mL, 34.52 mmol) in toluene. The reaction temperature was maintained at 0° C. for 2 h but little progress in the reaction was observed. Additional equivalents (7.6 mL) of DIBAL-H were added at 2 and 4 hours respectively. The DIBAL-H reagent was quenched with 1N HCl, and the quenched reaction mixture was extracted with dichloromethane (3×50 mL) and dried over Na2SO3. Evaporation of the solvent gave 38 g (70%) of Compound (6) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 3.42 (s, 3H), 3.74 (t, J=5.1, 9.9 Hz, 2H), 4.49 (t, J=4.8, 10.2 Hz, 2H), 4.67 (s, 2H), 5.29 (s, 2H), 7.29 (m, 3H), 7.39 (s, 1H). LCMS: m/z for C16H18BrN5O3++H observed 408.1 and 410.0 at 1.85 minutes of a 3.5 minute run, eluting 5-95% CH3CN in H2O (C18 column).

Provenance & Evidence