Ethylenediamine → N-(2-Aminoethyl)-2-[4-[2-(2,3,6,9-tetrahydro-1,3-dipropyl-2,6-dioxo-1H-purin-8-yl)propyl]phenoxy]-acetamide

Participants

Reaction Steps

Dissolve (+)-2-[4-[2-(2,3,6,9-tetrahydro-1,3-dipropyl-2,6-dioxo-1H-purin-8-yl)propyl]phenoxy]acetic acid (0.28 g, 0.65 mmol) in dimethylformamide (10 mL) and treat with N-hydroxysuccinimide (0.074 g, 0.65 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.262 g, 1.37 mmol). Stir for 1 hour and add a solution of ethylenediamine (10 mL of a 10% solution in methanol) and stir for 1 hour. Dilute with chloroform (500 mL), wash with 5% sodium carbonate (200 mL) and dry (MgSO4). Evaporate the solvent in vacuo and purify by radial chromatography (10→20% methanol/chloroform with 1% ammonium hydroxide). Dissolve the purified material in 5% methanol/ethyl ether and treat with ethereal hydrochloric acid. Evaporate the solvent in vacuo and triturate the residue with ethyl ether. Filter the resulting solid and dry to give the title compound (88 mg); [α]d 20 =+75.7° (C=0.96, H2O).

Provenance & Evidence