Sodium Hydroxide → 2-(4-(1-((2-aminoethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of (9H-fluoren-9-yl)methyl 2-((3-(4-(2-hydroxypropan-2-yl)phenyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)methoxy)ethylcarbamate (0.030 g, 0.040 mmol, Preparation #AW.1) in 1,4-dioxane (1 mL) was added NaOH (5.0 N aqueous, 0.040 mL, 0.20 mmol). The mixture was heated at about 70° C. for about 4 h. The mixture was then concentrated under reduced pressure, dissolved in MeOH/DMSO (1:1) (2 mL) and purified via reverse phase preparatory HPLC (Table 2, Method n). The desired fractions were collected and concentrated under reduced pressure. The residue was dissolved in water (4 mL) and lyophilized for 16 h to give 2-(4-(1-((2-aminoethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol (6.5 mg, 44%): LC/MS (Table 2, Method a) Rt=1.30 min.; MS m/z: 364 (M−H)−.

Provenance & Evidence