Dimethylamine → Cycloechinulin

Participants

Reaction Steps

O-(1H-Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (7.752 g, 20.48 mmol), 1-hydroxybenzotriazole (0.92 g, 6.8 mmol) and n,n-ethyldiisopropylamine (4.8 ml, 27.76 mmol) were added to a suspension of 5 (4.4 g, 13.6 mmol) in dichloromethane (200 ml). The solution was stirred for 30 min under nitrogen, dimethylamine (2M in THF, 9.33 ml, 28.0 mmol) added and the mixture stirred at room temperature for 3 hr. Dichloromethane (200 ml) was added, and the solution washed with HCl (0.5M), saturated NaCl solution, and 10% NaHCO3 solution. The organic phase was dried over MgSO4 and solvent evaporated to give a light cream solid methyl 3-dimethylcarbamoylmethyl-2-(4-tolyl)imidazo[1,2-a]pyridine-6-carboxylate 6 (3.2 g, 67%).

Provenance & Evidence