Imidazole → 3-(1H-imidazol-1-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

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Reaction Steps

Add sodium hydride (0.050 g; 2.2 equiv; 1.25 mmoles) to a solution of 3-chloropropyl 2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylate (0.22 g; 1.0 equiv; 0.57 mmoles) and 1H-imidazole (0.082 g; 2.1 equiv; 1.20 mmoles) in dimethylformamide (2 mL) and stir for 18 hours. Dilute the reaction with dichloromethane and water. Separate the layers and further extract the aqueous layer with dichloromethane (2×). Dry the combined organic extracts with sodium sulfate, filter, and concentrate. Purify the crude product by column chromatography (0 to 10% methanol in dichloromethane) to afford the desired 3-(1H-imidazol-1-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.078 g; 33%) as a white solid: MS (m/z): 419 (M+1).

Provenance & Evidence