Potassium Carbonate → tert-butyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(2-(tetrahydrofuran-2-yl)ethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A reaction mixture of 1-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (0.800 g, 2.17 mmol), tert-butyl 4-oxo-3-(3-(tetrahydrofuran-2-yl)propanoyl)piperidine-1-carboxylate (0.705 g, 2.17 mmol) and potassium carbonate (0.599 g, 4.33 mmol) in ethanol (6 mL) was stirred at 60° C. overnight. The reaction mixture was transferred to a microwave vial (20 mL) and run in the microwave at 120° C. for 45 minutes. The reaction mixture was filtered and washed with dichloromethane. The filtrate was concentrated and the residue was dissolved in dichloromethane and washed with water, dried (MgSO4) and concentrated. The crude product was purified by silica flash chromatography using a gradient of methanol in dichloromethane (0 to 4%) giving tert-butyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(2-(tetrahydrofuran-2-yl)ethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.335 g, 28.9%) as the product.

Provenance & Evidence