Sodium Carbonate → HCID 15949464, compound

Participants

Reaction Conditions

Reaction Steps

The toluene/ethanol (1/1) solvent mixture was deoxygenated vigorously with nitrogen gas prior to using in this reaction. A mixture of 4-[2-amino-4-(3-bromophenyl)-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile (173 mg, 0.465 mmol), sodium carbonate (148 mg, 1.394 mmol), pyrimidine-5-boronic acid (86.4 mg, 0.697 mmol) and tetrakis(triphenylphosphine)palladium(0) (27 mg, 0.023 mmol) in toluene/ethanol (1/1) solvent mixture (10 mL) was heated in a 100° C. oil bath for eight hours. TLC (5% methanol/chloroform) shows complete conversion to a new material. The solvent was removed by evaporation and the residue dissolved in chloroform and washed with water. The organic phase was dried (Na2SO4), filtered and evaporated. The resultant residue was purified by HPLC (Luna CN column, normal mobile phase). Crystallization from warm ethyl acetate/hexane afforded the title product as a pure crystalline material, mp 214-225° C.; MS (ES) m/z 370.1.

Provenance & Evidence