Trityl chloride → 2'-Deoxy-5'-O-(triphenylmethyl)uridine

Participants

Reaction Steps

2′-Deoxyuridine (1.00 g, 4.39 mmol) and triphenylmethylchloride (1.34 g, 4.83 mmol) were stirred in dry pyridine (20 ml) overnight at 50° C. under an atmosphere of nitrogen. The reaction mixture was then poured into ice-H2O (100 ml) with vigorous stirring and filtered. The precipitate was dissolved in EtOAc (100 ml) and the solution was washed with 0.5M HCl (100 ml) and H2O (100 ml), dried (Na2SO4) and reduced in vacuo. The residue was washed with toluene to leave the title compound (1.99 g, 97%) as a pale yellow solid. For analytical purposes, the compound was purified by gradient flash column chromatography, eluting with 5→10% MeOH/CHCl3.

Provenance & Evidence