Hydrochloric Acid → HCID 58382020, compound

Participants

Reaction Steps

tert-Butyl 7-ethyl-6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate (0.35 g, 0.631 mmol) in 1,4-dioxane (5 mL) was treated with TFA (0.073 mL, 0.946 mmol) then the solution was stirred for about 15 min at rt. The mixture was heated to about 60° C. for about 15 min and then TFA (0.145 mL, 1.88 mmol) was added and heating continued at about 75° C. for about 1 h. The solution was cooled to rt then concentrated (37%) aqueous HCl (0.083 mL, 1.015 mmol) was added. The mixture was stirred for about 15 min at rt then warmed to about 75° C. for about 4 h. The mixture was cooled then treated with saturated aqueous NaHCO3 (10 mL), EtOAc (25 mL) and water (10 mL). The layers were separated then the aqueous layer extracted with EtOAc (15 mL). The organics were combined then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The material was purified on a 10 g silica gel column with EtOAc as an eluent to give 1-(4-(2-amino-7-ethyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl)ethanone (0.217 g, 84%): LC/MS (Table 2, Method a) Rt=2.72 min; MS m/z 411 (M+H)+.

Provenance & Evidence