Imidazole → HCID 68699325, compound

Participants

Reaction Steps

Imidazole (0.183 g, 2.69 mmol) was added to a solution of 2′-deoxyuridine (0.272 g, 1.19 mmol) in dry DMF (5 mL) under nitrogen. The mixture was cooled in an ice-salt bath before drop-wise addition of triisopropylsilyl chloride (0.28 mL, 1.31 mmol) via a syringe. The reaction mixture was kept at 0° C. for 3 h, allowed to warm up to room temperature and then stirred at room temperature for 22 h. After addition of water (5 mL), the crude mixture was extracted with CHCl3 (2×10 mL). The organic layers were combined and dried over MgSO4. Removal of the solvent under reduced pressure afforded a crude transparent oil which was further purified by flash chromatography eluting the column (ISOLUTE SI) a gradient of 0→10% CH3OH in CHCl3. The title compound was obtained from the fractions with Rf=0.25 (10% CH3OH in CHCl3) as a crystalline white solid (0.366 g, 74%). M.p. 152-153° C.

Provenance & Evidence