Trimethylsilyl iodide → HCID 58010167, compound

Participants

Reaction Steps

To a solution of ethyl (1S,2R,4S,5R)-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[3.1.0]hexan-2-ylcarbamate (0.16 g, 0.34 mmol, prepared using GG from Preparation #KK.1, A from Preparation #9 with HATU and TEA, C with TEA) in DCM (2.3 mL) was added trimethylsilyl iodide (0.11 mL, 0.75 mmol). After stirring at ambient temperature for about 24 h, additional trimethylsilyl iodide (0.11 mL, 0.75 mmol) was added and the reaction mixture was heated to about 40° C. for about 4 days. The reaction mixture was cooled to ambient temperature, followed by the addition of saturated aqueous NaHCO3 (20 mL). The mixture was stirred for about 5 min and the layers were separated. The aqueous layer was further extracted with DCM (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to afford (1S,2R,4S,5R)-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[3.1.0]hexan-2-amine that contained 1 molar equiv DCM (0.17 g, 100%): LC/MS (Table 2, Method a) Rt=1.76 min; MS m/z: 409 (M+H)+.

Provenance & Evidence