Tetrahydrofuran → 1-{4-Chloro-6-[2-(2,4-dichloro-phenyl)-ethylamino]-pyrimidin-2-yl}-ethane-1,2-diol

Participants

Reaction Steps

To a solution of (6-chloro-2-vinyl-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine (240 mg, 0.73 mmol) in THF (2 mL), acetone (2 mL) and water (2 mL) is added 4-methylmorpholine N-oxide (342 mg, 2.92 mmol) followed by osmium tetroxide (153 μL, 0.015 mmol). After stirring the mixture at room temperature for 17 hours a solution of sodium bisulfite (728 mg, 7 mmol) in water (15 mL) is added and extracted twice with EtOAc (25 mL). The organic extracts are combined and dried over magnesium sulfate, filtered and concentrated to afford 1-{4-chloro-6-[2-(2,4-dichloro-phenyl)-ethylamino]-pyrimidin-2-yl}-ethane-1,2-diol (320 mg) as a solid.

Provenance & Evidence