2-Chloroquinoline-3-boronic acid → 2-Chloro-3-(2-methyl-9-(tetrahydro-2H-pyran-2-YL)-9H-purin-6-YL)quinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (0.55 g, 2.18 mmol), 2-chloroquinolin-3-ylboronic acid (0.90 g, 4.35 mmol, Aldrich, St. Louis, Mo.) and tetrakis(triphenylphosphine)palladium(0) (0.13 g, 0.11 mmol, Strem Chemicals, Inc., Newburyport, Mass.) in dioxane (3 mL) and water (1 mL) was sealed and purged with argon for several minutes. The reaction mixture was stirred at 90° C. for 6 h and then allowed to cool to room temperature. The organic phase was taken and the solvents removed under vacuum. Purification of the crude reaction mixture by silica gel chromatography (0 to 3% MeOH/CH2Cl2) provided the title compound as an orange solid. m/z (ESI, +ve ion) 380 (M+H)+.

Provenance & Evidence