Triisopropyl borate → 4-Chloro-7-cyclopentyl-5-(2-phenoxyphenyl)pyrrolo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-7-cyclopentyl-5-iodopyrrolo[2,3-d]pyrimidine (1.26 g) and potassium (2-phenoxyphenyl)trifluoroborate (1.0 g, prepared by reacting 2-phenoxybromobenzene with butyllithium in tetrahydrofuran at -70° C. followed by triisopropyl borate (IV) followed by potassium hydrogen fluoride by a method analogous to that described in J. Org. Chem. 1995, 60, 3020-3027), in degassed toluene (40 ml), ethanol (10 ml) and water (10 ml) was stirred under nitrogen and bis(triphenylphosphine)palladium (II) chloride (0.25 g) was added followed by sodium bicarbonate (2.0 g). The mixture was stirred and heated at 105° C. for 16 hours and then cooled to ambient temperature. The mixture was separated and the upper layer was evaporated under reduced pressure to give a residue which was purified by flash column chromatography on silica using petroleum ether/ether (2:1) as a mobile phase to give 4-chloro-7-cyclopentyl-5-(2-phenoxyphenyl)pyrrolo[2,3-d]pyrimidine which was used directly in the next part of this example.

Provenance & Evidence