1,2-Dimethoxyethane → HCID 178420863, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 6-chloro-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (0.525 g, 2 mmol), 5-bromo-2-fluoropyridine-3-boronic acid (0.5 g, 2 mmol) (Alfa Aesar, Ward Hill, Mass.), potassium carbonate (0.5 g, 9 mmol), (Aldrich, St. Louis, Mo.) dichloro[1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(II) dichloromethane adduct (0.2 g, 0.2 mmol) (Strem Chemicals, Inc., Newburyport, Mass.). A deoxygenated mixture of 1,2-dimethoxyethane (10 mL, 96 mmol) (Aldrich, St. Louis, Mo.) and water (1 mL) was added. The vial was deoxygenated for 5 minutes, capped, and the reaction mixture was stirred at 100° C. for 2 h. The crude product was adsorbed onto a plug of silica gel and chromatographed through a RediSep®, Teledyne ISCO, Lincoln, Nebr., pre-packed silica gel column (120 g), eluting with a gradient of 20% to 80% ethyl acetate in hexane to provide 6-(5-bromo-2-fluoropyridin-3-yl)-2-methyl-9-(tetrahydro-2-H-pyran-2-yl-9H-purine. m/z (ESI, +ve) 392/394 (M+H)+.

Provenance & Evidence