Sodium hydride → 9-((3-phenylbenzo[b]thiophen-2-yl)methyl)-9H-purin-6-amine

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Reaction Steps

NaH (60% in mineral oil, 15 mg, 0.377 mmol) was added in one portion to a mixture of 9H-purin-6-ylamine (47 mg, 0.345 mmol) in DMF (3 mL) at RT. After 5 min stirring, a solution of methanesulfonic acid 3-phenylbenzo[b]thiophen-2-ylmethyl ester from Example 26 (100 mg, 0.314 mmol) in DMF (2 mL) was added dropwise and stirring at RT was continued for 30 min. The reaction mixture was then quenched by addition of water and a solid formed. The precipitated was collected by filtration and was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in EtOAc) and triturated from diethyl ether affording 166 as a white solid (52 mg, 46%). LCMS: RT 3.99 min [M+H]+ 358.1. 1H NMR (DMSO, 400 MHz): δ 8.15 (1H, s), 8.06 (1H, s), 7.98-7.92 (1H, m), 7.64-7.59 (4H, m), 7.57-7.46 (2H, m), 7.42-7.37 (2H, m), 7.27 (2H, s), 5.63 (2H, s)

Provenance & Evidence