Triethylamine → HCID 59311451, compound

Participants

Reaction Steps

The above di-tert-butyl {4-chloro-3-(2-hydroxyethyl)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl}imidodicarbonate (8.5 g) was dissolved in dichloromethane (100 ml), triethylamine (4.5 ml) was added. Methanesulfonyl chloride (1.9 ml) was added under cooling in an ice bath, and the mixture was stirred at room temperature for two hours. The reaction solution was diluted with dichloromethane and ethyl acetate and washed with water. Then, the organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in N,N-dimethylformamide (100 mL), and sodium bisulfide monohydrate (1.5 g) was added under cooling in an ice bath. Then, the ice bath was removed and the mixture was stirred for one hour. Potassium carbonate (3.3 g) was added to the reaction mixture, followed by further stirring for 16 hours. Water (1000 ml) was added to the reaction mixture, followed by extraction with dichloromethane (500 ml) twice. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the title compound (6.0 g, 74%) as an oil.

Provenance & Evidence