Sodium periodate → HCID 54765062, compound

Participants

Reaction Steps

To a solution of N-[4-(4-fluorophenyl)-5-(1-hydroxybut-3-enyl)-6-isopropyl-pyrimidin-2-yl]-N-methylmethanesulfonamide (2 g, 5.08 mmol) in a mixture of 30 mL methanol and 4 mL buffer solution (pH=7), sodium periodate (3.2 g, 15.2 mmol) and osmium tetroxide (0.3 mL, 4% wt. in water, 13 mg) are added at room temperature. The reaction mass is stirred and the progress of the reaction is monitored by TLC. Upon completion of the reaction, the reaction mixture is filtered through celite bed (1 g) and washed with ethyl acetate (2×10 mL). The filtrate is distilled under reduced pressure until solvents are removed. To the residue, ethyl acetate (200 mL) is added and washed with DM water (50 mL) and brine (50 mL), subsequently. The solvent is distilled off under reduced pressure to afford 2.1 g crude product. Part of the residue (200 mg) is purified through silica gel column chromatography eluting with (20%-30%) ethylacetate:cyclohexane to obtain 60 mg pure N-(4-(4-fluorophenyl)-5-(1-hydroxy-3-oxopropyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide.

Provenance & Evidence