Bromine → ethyl (3-((6-amino-8-bromo-2-butoxy-9H-purin-9-yl)methyl)phenyl)methyl(methyl)phosphinate

Participants

Reaction Steps

To a solution of 68 (204.0 mg, 0.488 mmol) in CHCl3 (5 mL) was added a 10% (v) solution of Br2 in chloroform. The reaction was stopped when starting material was consumed, monitored by HPLC. Bromine was quenched with a saturated Na2SO3 solution and product extracted with DCM (2×10 mL). Organics were washed with water (2×10 mL) and brine (1×10 mL) and dried over Na2SO4. Purified by flash column eluting 10% methanol in ethyl acetate. Evaporation of solvent gave 130.4 mg (54%) of 69 as a yellow solid. LCMS: m/z for C20H27BrN5O3P++H observed 496.2 and 498.1 at 2.18 minutes of a 3.5 minute run, eluting 5-95% CH3CN in H2O.

Provenance & Evidence