Dimethylamine → HCID 58382209, compound

Participants

Reaction Steps

A flask was charged with (6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (0.413 g, 0.944 mmol, Preparation #1.1), CDI (0.184 g, 1.13 mmol), DIEA (0.412 mL, 2.36 mmol) and THF (10 mL). The mixture was allowed to stir at rt for about 1 h. Dimethylamine (2.0 M in THF, 0.472 mL, 0.944 mmol) was added to the mixture. After about 4 h, additional dimethylamine (2.0 M in THF, 0.236 mL, 0.472 mmol) was added. After about 12 h, dimethylamine (2.0 M in THF, 0.236 mL, 0.472 mmol) was added. After about 8 h, the mixture was concentrated under reduced pressure and the residue was dissolved in DCM (10 mL). The organic solution was then washed with water (2×4 mL). The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 0 to 10% MeOH/DCM to give 3-((6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)-1,1-dimethylurea (0.114 g, 24%): LC/MS (Table 2, Method b) Rt=2.62 min; MS m/z 509 (M+H)+.

Provenance & Evidence