Sodium Hydroxide → HCID 86711290, compound

Participants

Reaction Steps

(R)-tert-Butyl (5-(4-amino-6-bromo-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pent-1-en-3-yl)carbamate (994 mg) obtained in Step 7 was added to a solution of 9-borabicyclo[3.3.1]nonane in 0.5 M THF (22.8 ml) at room temperature. The mixture was stirred at the same temperature for 1 hour, and a 4 N aqueous sodium hydroxide solution (5.7 ml) was carefully added thereto. After nitrogen purging, the mixture was heated to have an internal temperature of 55° C. Tetrakis(triphenylphosphine)palladium (275 mg) was added thereto, and the mixture was stirred at an internal temperature of 66° C. for 15 hours. After cooling the reaction mixture, the organic layer was separated, and toluene (7.7 ml) and a 20% aqueous ammonium chloride solution (5 ml) were added thereto. The organic layer was separated, washed with a 20% saline solution, and SH silica gel (produced by Fuji Silysia, 1 g) was added thereto. The mixture was stirred at an internal temperature 68° C. for 1 hour, and SH silica gel (produced by Fuji Silysia, 1 g) was added thereto. The mixture was stirred at an internal temperature of 68° C. for 1 hour. After cooling, the silica gel was filtered off, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/methanol) to obtain the title compound as a yellow solid (439 mg).

Provenance & Evidence