Hydrochloric Acid → 4-(1,4-diazepan-1-yl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile

Participants

Reaction Steps

To a solution of tert-butyl 4-{3-cyano-2-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propyl}-1,4-diazepane-1-carboxylate (6.4 g, 11 mmol;) in DCM (10 mL) was added 4.0 M of hydrogen chloride in 1,4-dioxane (22 mL, 88 mmol). The reaction solution was stirred at room temperature for 90 minutes. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. The organic layer was washed with 1.0 N NaOH solution. The aqueous was extracted with ethyl acetate. The combined extracts were dried over MgSO4, filtered, and concentrated to give the desired product as a brown sticky gum (4.1 g, 77%). LCMS calculated for C24H37N8OSi(M+H)+: m/z=481.2.

Provenance & Evidence