Sodium ethoxide → tert-Butyl 2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-4-(1-phenylethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

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Reaction Steps

1-(4-(2-Methyl-1H-imidazol-1-yl)phenyl)guanidine (700 mg, 3.25 mmol, example 9e), tert-butyl 4-oxo-3-(2-phenylpropanoyl)piperidine-1-carboxylate (1293 mg, 3.90 mmol) and sodium ethoxide (221 mg, 3.25 mmol) in ethanol (6 mL) were heated to 110° C. in a microwave reactor for 4 h. The solvent was evaporated and the crude was dissolved in ethyl acetate and washed with water. The organic phase was dried under MgSO4 and the solvent was evaporated under reduced pressure. Purification by flash chromatography using dichloromethane and methanol (0-10%) as eluent gave tert-butyl 2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-4-(1-phenylethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (612 mg, 36.9%). MS (ES+) m/z 511 (M+H)+

Provenance & Evidence