Trimethylsilyl triflate → 2-Methyl-1-(2',3'5'-tri-o-benzoyl-beta-d-ribofuranosyl)-pyrimidin-4-one

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Reaction Steps

2-Methylpyrimidin-4-one (4.42 g, 40 mmol) and a few crystals of ammonium sulfate were refluxed in HMDS overnight. After cooling to room temperature the colorless solution was evaporated. A solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribose (40 mmol, 20.18 g) in 1,2-dichloroethane (200 ml) was added to the residue. Trimethylsilyl trifluoromethanesulfonate (TMSOTfl, 9.78 g, 44 mmol) was added and the resulting clear solution was stirred at room temperature for 2 hrs. The reaction mixture was poured in to saturated NaHCO3 (300 ml) and extracted with chloroform (2×200 ml). The organic phase was evaporated to give a colorless homogeneous foam (23.04 g, 104%, pure by NMR).

Provenance & Evidence