Sodium Thiosulfate → HCID 178507660, compound

Participants

Reaction Steps

In a reaction vessel, {2,4-difluoro-3-[hydroxy-(4-hydroxy-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-carbamic acid methyl ester (38, 690 mg, 1.97 mmol) is dissolved in 200 mL of tetrahydrofuran and Dess-Martin periodinane (877.3 mg, 2.068 mmol) is added. The resulting mixture is stirred at room temperature for 3 hours, then 20 mL of saturated aqueous sodium bicarbonate, 5 mL of saturated aqueous sodium thiosulfate, and 100 mL of ethyl acetate are added for extraction. The organic layer is isolated and the aqueous layer extracted with 50 mL of ethyl acetate. The organic fractions are combined and washed with water, then brine, dried with magnesium sulfate, filtered and the filtrate is concentrated under vacuum. The resulting material is suspended in acetonitrile, sonicated for 1 hour, then filtered to collect the solid material, which is then washed with acetonitrile. The resulting material is suspended in 15 mL of dioxane, and combined with 15 mL of 10N aqueous sodium hydroxide, and heated to reflux for 5 hours. The reaction mixture is adjusted to approximately pH 6 with 6N hydrochloric acid and extracted with ethyl acetate. The organic layer is concentrated under vacuum and the resulting material purified by silica gel chromatography eluting with methanol and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (39, 287 mg). MS (ESI) [M−H+]−=289.1.

Provenance & Evidence