Sodium hydride → HCID 59489502, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (4-(benzo[4,5]imidazo[1,2-a]pyrimidin-4-yl)phenyl)carbamate (300 mg, 0.83 mmol) in DMF (9 mL) at 0° C. was added NaH (38 mg, 0.91 mmol, 60% dispersed in oil). After stirring for 5 min at 0° C. for 5 min, ice bath was removed and reaction was stirred at rt for 20 min. The reaction was cooled again at 0° C. and propane-1,3-diyl bis(4-methylbenzenesulfonate) (653 mg, 1.7 mmol) was added in 6 portions. After stirring at 0° C. for 5 min, the reaction was let stir at rt for 2 h and quenched with saturated NH4Cl solution (40 mL). The mixture was extracted with DCM (3×30 mL). The combined organic phase was washed with water (2×50 mL) and dried over MgSO4 and concentrated. The residue was first purified by silica chromatography (THF in DCM, 0% to 18%) and then reversed phase HPLC (TFA buffered water/MeCN) to afford the title compound as an orange solid (160 mg, 34%). MS (ESI) m/z [M+H]+573.

Provenance & Evidence