Acetone → 9-((2-Phosphonylmethoxy)ethyl)guanine

Participants

Reaction Steps

Bromotrimethylsilane (2.77 g, 18.1 mmol) was added dropwise over 2 min to a solution of 9-(2'-(diethylphosphonomethoxy)ethyl)guanine (0.625 g, 1.80 mmol) in 15 mL of dry DMF at rt under argon in a foil-covered flask. The reaction mixture was stirred at rt for 4 h and then volatiles were removed in vacuo to give a viscous yellow oil. The residue was treated with 5 mL of water, giving immediate formation of a white solid. 5 mL more water was added, followed by 10 mL of acetone; the precipitate was collected by filtration. The crude product was purified by recrystallization from water/ethanol to give 0.483 g of 9-(2-(phosphonomethoxy)ethyl)guanine as white crystals, m.p. >260°.

Provenance & Evidence