Acetaldehyde → HCID 58382478, compound

Participants

Reaction Steps

To a flask was added 2-hydrazinyl-6-(1-methyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (0.100 g, 0.278 mmol, Preparation #P.2.1) and acetaldehyde (0.079 mL, 1.3 mmol) in DCM (3 mL). The mixture was stirred at rt for about 90 min. The mixture was concentrated in vacuo to give a residue. The residue was transferred to a flask and copper(II) chloride (0.075 g, 0.56 mmol) in DMF (3 mL) was added. The mixture was heated to about 90° C. for about 2 h. The mixture was cooled to rt, diluted with ice water (50 mL) and the solid was collected by filtration. The solid was taken up in DCM/MeOH and the insoluble solids were collected by filtration while the mother liquor was purified by flash chromatography (25 g silica gel column, DCM/EtOAc/MeOH 1:0:0 to 0:1:0 to 9:0:1) to give a solid. The solids were combined to give 1-methyl-7-(1-methyl-1H-pyrazol-4-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.04 g, 37%): LC/MS (Table 2, Method c) Rt=1.48 min; MS m/z 384 (M+H)+.

Provenance & Evidence