6-Chloropurine → HCID 178463552, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-[5-fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethanamine (0.39 g, 1.4 mmol, 6-chloropurine (0.27 g, 1.8 mmol) and sodium hydrogenecarbonate (0.17 g, 2.0 mmol) in 1-butanol (4 mL) was heated at 110° C. overnight. The mixture was filtered and purified on a preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at a flow rate of 30 mL/min) to give the desired product. LCMS calculated for C22H17F2N6 (M+H)+: m/z=403.1; Found: 403.1. The racemic N-{1-[5-fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethyl}-9H-purin-6-amine (70 mg, 0.2 mmol) was submitted for chiral resolution (column: ChiralPak IA, 20×250 mm, 5 μm; mobile phase: 15% ethanol/85% hexanes; flow rate: 15 mL/min) to give two enantiomers. retention times: 8.7 and 13.5 minutes, respectively.

Provenance & Evidence