Cesium carbonate → N-(3-(6-Amino-8-((6-iodo-2,3-dihydro-1H-inden-5-yl)thio)-9H-purin-9-yl)propyl)-2-methylpropane-2-sulfinamide

Participants

Reaction Steps

To a solution of 8-((6-iodo-2,3-dihydro-1H-inden-5-yl)thio)-9H-purin-6-amine (13 mg, 0.03 mmol) in DMF (1.5 mL) was added N-(3-bromopropyl)-2-methlpropane-2-sulfinamide (23 mg, 0.1 mmol) and Cs2CO3 (21 mg, 0.06 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was condensed under vacuum and the residue was purified by Prep TLC (CH2Cl2:NH3-MeOH (7N), 20:1) to yield WS63 as a white solid (5 mg, 27%). 1H NMR (600 MHz, CDCl3): δ 8.22 (s, 1H), 7.68 (s, 1H), 7.05 (s, 1H), 5.70 (br s, 2H), 4.83 (t, J=6.7 Hz, 1H), 4.28-4.36 (m, 1H), 4.17-4.27 (m, 1H), 2.99-3.07 (m, 1H), 2.85-2.93 (m, 1H), 2.81 (t, J=7.4 Hz, 2H), 2.72 (t, J=7.5 Hz, 2H), 1.83-2.08 (m, 4H), 1.20 (m, 9H); HRMS (ESI) m/z [M+H]+ calcd. for C21H28IN6OS2, 571.0811. found 571.0809.

Provenance & Evidence