8-ethyl-7-(4-heptyl)-3-(4-methoxybenzyl)-1-methyl-3,7-dihydro-1H-purine-2,6-dione → HCID 11150504, compound

Participants

Reaction Steps

A solution of 8-ethyl-7-(4-heptyl)-3-(4-methoxybenzyl)-1-methyl-3,7-dihydro-1H-purine-2,6-dione in trifluoroacetic acid was heated at 100° C. in a sealed tube for 8 h. The mixture was cooled to r.t. and concentrated. The residue was transferred into a separatory funnel containing saturated aqueous NaHCO3 (20 mL) and the aqueous layer was extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel (5% methanol in CH2Cl2) to afford a colorless solid (645 mg, 91% yield): mp 152.5–153° C.; 1H NMR (300 MHz, CDCl3) δ 12.0 (s, 1H), 4.20–4.10 (m, 1H), 3.41 (s, 3H), 2.94 (q, J=7.3 Hz, 2H), 2.33–2.19 (m, 2H), 1.94–1.83 (m, 2H), 1.42 (t, J=7.4 Hz, 3H), 1.26–1.06 (m, 4H), 0.90 (t, J=7.3 Hz, 6H); LRMS (APCI) m/e 293.1 [(M+H)+, calcd for C15H25N4O2 293.2].

Provenance & Evidence