Sodium hydride → HCID 58071998, compound

Participants

Reaction Conditions

Reaction Steps

174 mg (R)-4-Hydroxymethyl-1-((R)-1-phenyl-ethyl)-imidazolidine-2-one (2.28) was placed in 2 mL dimethylacetamide under nitrogen at ambient temperature before 37.8 mg sodium hydride (60% dispersion in oil) was added. The reaction was stirred for 10 min and then 296 mg 5-chloro-7-(3,4-dimethoxy-phenyl)-[1,6]naphthyridine (6.37) as a solution in 2 mL dimethylacetamide was added. The mixture was heated to 90° C. where it was maintained for 2 h. After this time additional sodium hydride was added and the reaction was stirred at 90° C. for a further 16 h and then at ambient temperature for 3 d. After this time the reaction was heated to 90° C. for 24 h and then it was cooled to ambient temperature. The reaction was quenched by the addition of 5 mL water and extracted with ethyl acetate (×3). The organic fractions were combined, dried over sodium sulfate, filtered and the solvent was removed from the filtrate under reduced pressure. Purification by silica gel chromatography (ethyl acetate/dichloromethane: 5-7% then switching to methanol/ethyl acetate: 10%) provided the title compound.

Provenance & Evidence