Benzyl azide → HCID 44200196, compound

Participants

Reaction Steps

A solution of 1-(2-ethynyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one (0.100 g, 0.44 mmol), benzyl azide (0.055 mL, 0.44 mmol), CuSO4 (0.007 g, 0.04 mmol), and L-ascorbic acid (0.078 g, 0.44 mmol) in 3 mL of tert-butanol and 3 mL of water was stirred for 1.5 h, then diluted with 30 mL of water and extracted with 100 mL of ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated to a residue. Silica gel chromatography (0->50% EtOAc/hexanes) afforded 0.036 g (23%) of 1-[2-(1-benzyl-1H-[1,2,3]triazol-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as an off-white solid. MS: 361 M+1, M.P. 235.0-237.0° C.

Provenance & Evidence