Water → HCID 58180888, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 2-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanoate (1.0 g, 2.3 mmol) in toluene (10 mL, 90 mmol) was cooled at −78° C. 1.0 M of Diisobutylaluminum hydride in toluene (2.8 mL, 2.8 mmol) was added dropwise over 10 minutes. Another 1.0 M of diisobutylaluminum hydride in toluene (3.0 mL, 3.0 mmol) was added. The mixture was warmed to −55° C. After quenching with 2.8 M of sodium hydroxide in water (10 mL, 30 mmol), the mixture formed an emulsion. Ethyl acetate was then added, and the aqueous phase was extracted with ethyl acetate. The combined organic layer was washed with 2.8 M of sodium hydroxide in water, water, saturated NH4Cl, and saturated NaCl. The organic phase was dried and the solvent was evaporated by rotary evaporation at 35° C. to give an orange oil. The orange oil was then twice redissolved in toluene and then the solvent was removed by rotary evaporation to give 0.8 g orange oil (90% yield). LCMS: 386.

Provenance & Evidence