Ammonium Chloride → HCID 58382382, compound

Participants

Reaction Conditions

Reaction Steps

1-(4-(8-Ethyl-1-methyl-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-7-yl)phenyl)ethanone (0.092 g, 0.205 mmol, Preparation #W.1) in THF (5 mL) was cooled to about −20° C. and MeMgCl (3.0 M in THF, 0.1 mL, 0.3 mmol) was added. After about 5 min MeMgCl (3.0 M in THF, 0.1 mL, 0.3 mmol) was added then the mixture was warmed to about 0° C. MeMgCl (3.0 M in THF, 0.2 mL, 0.6 mmol) was added and the mixture was allowed to warm to about 15° C. over about 2 h. MeMgCl (3.0 M in THF, 0.2 mL, 0.600 mmol) was added to THF (3 mL) and the solution was added to the mixture portion-wise. An aqueous solution of NH4Cl (4 mL) was added slowly. The mixture was diluted with water (20 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer was extracted with EtOAc (15 mL). The combined organics were dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 2-(4-(8-ethyl-1-methyl-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-7-yl)phenyl)propan-2-ol (0.108 g, 113%): LC/MS (Table 2, Method a) Rt=2.96 min.; MS m/z 465 (M+H)+.

Provenance & Evidence