Triphenylphosphine → HCID 58739260, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (1-trityl-1H-[1,2,4]triazol-3-yl)-methanol (320 mg, 0.47 mmol) and triphenylphosphine (136 mg, 0.47 mmol) in tetrahydrofuran (9.4 mL) cooled to 0° C. was treated with diethylazodicarboxylate (0.82 mL, 0.47 mmol). This solution was warmed to 25° C. for 5 min and then was re-cooled to 0° C. where it was stirred for an additional 10 min. At this time, the reaction was treated with 2-(4-acetylamino-phenyl)-N-[6-amino-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetamide (200 mg, 0.47 mmol). The reaction was then allowed to slowly warm to 25° C. The resulting solids were removed by filtration. The filtrate was diluted with ethyl acetate, washed with water and a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh) afforded 2-(4-acetylamino-phenyl)-N-[6-amino-3-(2-fluoro-benzyl)-2,4-dioxo-1-(1-trityl-1H-[1,2,4]triazol-3-ylmethyl)-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetamide (55 mg, 15.6%) as a yellow foam: LR-APCI for C43H37FN8O4 (M+H)+at m/z=749.

Provenance & Evidence