3-Pentanamine → {(1S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-cyclopent-2-enyl}-propionyl-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

[(1S,4R)-4-(2,6-Dichloro-purin-9-yl)-cyclopent-2-enyl]-propionyl-carbamic acid tert-butyl ester (700 mg, 1.64 mmol) is dissolved in THF (15 ml) under an atmosphere of argon. 3-Pentyl-amine (315 mg, 3.61 mmol) is added and the reaction mixture is stirred at 50° C. The reaction is shown to be complete by LCMS after 18 hours. The reaction mixture is partitioned between dichloromethane (50 ml) and 0.1M HCl (50 ml). The organic layer is washed with water (20 ml) and brine (20 ml), dried over MgSO4, filtered and the solvent is removed in vacuo to give the title compound. 1H nmr (CDCl3, 400 MHz); 8.10(s, 1H), 6.00(m, 1H), 5.70(m, 1H), 5.60(m, 2H), 5.45(m, 1H), 4.20(m, 1H), 3.65(m, 1H), 3.00(m, 1H), 2.65(m, 3H), 1.95(m, 1H), 1.60(m, 3H), 1.45(s, 9H), 1.10(m, 4H), 0.85(t, 6H), MS (ES+) m/e 477 (MH+).

Provenance & Evidence