Isopropyl iodide → 9-(4-Chlorophenyl)-8-(2-chlorophenyl)-6-isopropoxy-9H-purine

Participants

Reaction Steps

9-(4-Chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-ol (I-(4A-7)b; 50 mg, 0.14 mmol), 2-iodopropane (26 mg, 0.15 mmol), and cesium carbonate (50 mg, 0.15 mmol) were combined in dimethylformamide (0.7 ml) and stirred overnight. Additional 2-iodopropane (13 mg, 0.76 mmol), and cesium carbonate (25 mg, 0.76 mmol) were added and stirred an addional day. The reaction mixture was diluted with ethyl ether and then washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried (Na2SO4), evaporated to dryness, and then purified on a Biotage™ Flash 12S column using 0–70% ethyl acetate in hexanes as eluant to afford title compound 31A-1 (34 mg, 56%); 1H NMR: +ESI MS (M+1) 399.4; (400 MHz, CD2Cl2) δ 8.51 (s, 1H), 7.56 (dd, J=7.5, 1.7 Hz, 1H), 7.47–7.34 (m, 5H), 7.23 (d, J=9.1 Hz, 2H), 5.71 (septuplet, J=6.2 Hz, 1H), 1.50 (d, J=6.2 Hz, 6H).

Provenance & Evidence