Iodoethane → HCID 13606735, compound

Participants

Reaction Steps

To a stirred solution of 9-(1,3-dihydroxy-2-propoxymethyl)guanine (766 mg, 3.0 mmol) in sieve-dried DMSO (4 ml), under N2, was added 120 mg of 60% NaH in oil (i.e. 72 mg NaH, 3.0 mmol). Hydrogen evolution ceased and a clear solution was obtained after 10 minutes. Ethyl iodide (491 mg, 3.15 mmol) in DMSO (1 ml) was added over approximately 1 minute. The reaction was stirred overnight and then poured into CH2Cl2. The gummy precipitate was filtered off and triturated under methanol to give crystalline material. This was dissolved in MeOH--H2O (2:3) and applied to a Dowex 1×2 column (OH- form, 100 ml) packed in the same solvent. The column was developed in MeOH--H2O (2:3) and fractions containing the required product were pooled and evaporated to dryness. This residue was crystallized from methanol to give 230 mg (27% yield) of product.

Provenance & Evidence