1,3-Propanediamine → 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-(3-aminopropyl)propanamide

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Reaction Steps

0.250 g (1.06 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) was added to 1.85 g (25.0 mmol) of 1,3-diaminopropane in a 10 ml round bottom flask equipped with a magnetic stirring bar. The solution was stirred at room temperature for two hours. 10 ml ether was added and the solution was stirred for a few minutes. The ether solution was decanted, leaving an oil residue. 5 ml of acetonitrile and 4 ml of ether were added and the solution was stirred. Methanol was added dropwise until a precipitate had formed. The solution was filtered and washed with acetonitrile and ether, to yield 205 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-(3-aminopropyl)propanamide (AIT-0074). m.p. 172°-175° C. Yield: 73%

Provenance & Evidence