Imidazole → HCID 10451163, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-fluoro-2′-deoxyuridine (FDUR) (4.92 g, 20 mmol) in pyridine (100 mL) was added DMTrCl (10.16 g, 30 mmol) portion-wise at 0° C. and the solution was stirred at 0° C. for 2 h. Water (5 mL) was added and the mixture was evaporated to dryness and the residue was co-evaporated with toluene (2×20 mL). The residue was dissolved in EtOAc (200 mL) and the solution was washed with brine and dried over Na2SO4. Solvent was removed and the residue was dissolved in CH2Cl2 (100 ml). To the solution were added imidazole (4.08 g, 60 mmol) then t-butyldimethylsilylchloride (TBSCl, 4.52 g, 30 mmol) and the mixture was stirred at room temperature for overnight. Water (50 mL) was added and the mixture was evaporated to dryness. The residue was dissolved in EtOAc (300 mL) and the solution was washed with brine and dried over Na2SO4. Solvent was removed and the residue was co-evaporated with toluene twice then dissolved in CH2Cl2 (200 mL). To the solution was added trifluoroacid (TFA, 3 mL) and the solution was stirred at room temperature for 3 h. Water (5 mL) was added and the mixture was stirred for 30 min then methanol (10 mL) added. After 10 min, the solution was neutralized with 30% ammonium hydroxide. The mixture was concentrated to dryness and the residue was purified by silica gel chromatography to give product as solid (5.6 g. 78%). 1H-NMR (CDCl3): δ 8.88 (br s, 1H), 7.96 (d, J=6.4 Hz, 1H), 6.23 (m, 1H), 4.78 (m, 1H), 3.95 (m, 1H), 3.79 (m, 1H), 2.28 (m, 2H), 0.88 (s, 9H), 0.00, 0.09 (ss, 6H). LC-MS (ESI): 361 [M+1]+.

Provenance & Evidence