Tetrahydrofuran → HCID 118598658, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of sodium hydride (50% dispersion washed free of mineral oil, 90 mg, 1.87 mmol) in dimethylsulfoxide (2 mL) is heated to 65° C. under argon for 1 h. The oil bath is removed and to the clear solution is added tetrahydrofuran (2 mL). The solution is cooled to −15° C. and treated with a solution of trimethylsulfonium iodide (0.35 g, 1.72 mmol) in dimethylsulfoxide (2 mL). After 3 min a solution of 2′-(4-methoxybenzyl)-6′-((4-methoxybenzyl)(pyrimidin-4-yl)amino)-1′,5′-dioxo-1′,5′-dihydro-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-8′-carbaldehyde (4, 1 g, 1.72 mmol) in 3 ml. of tetrahydrofuran is added. The reaction is stirred overnight. The resulting mixture is poured into water and extracted with ethyl acetate. The extracts are washed with water, dried and evaporated to afford 2′-(4-methoxybenzyl)-6′-((4-methoxybenzyl)(pyrimidin-4-yl)amino)-8′-(oxiran-2-yl)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (5).

Provenance & Evidence