Toluene → HCID 22844874, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 10 (0.25 g, 0.6 mmol), 2,6-dichloropurine (0.142 g, 0.75 mmol) in 10 mL acetonitrile was cooled to 0° C. and a 1.8 M toluene solution of diethyl aluminum chloride (0.345 mL, 0.62 mmol) was added over 1 min. Stirring was continued at 0° C. for 5 minutes and at 25° C. for 10 minutes. The reaction mixture was quenched by pouring into a mixture of 20 mL dichloromethane and 10 mL saturated NaHCO3. The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was flash chromatographed with 15:1 toluene/ethyl acetate. Solvent removal gave 98 mg (30%) of 12. FAB MS 543 (M+H)+ ; 1H NMR (CDCl3) δ 8.47 (s, 1, H-8), 7.7 (m, 4, ArH), 7.45 (m, 6, ArH), 6.22 (m, 1, 1'-H), 3.96 (m, 1, 5'-H), 3.85 (m, 2, 4'-H, 5'-H), 2.45 (m, 2, 2'-H's), 2.25 (m, 1, 3'-H), 1.82 (m, 1, 3'-H), 1.1 (s, 9, t-butyl).

Provenance & Evidence