Triphenylphosphine → N-(2,4-dimethylphenyl)-4-((2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)methoxy)-N-isobutylbenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(2,4-dimethylphenyl)-4-hydroxy-N-isobutylbenzenesulfonamide (33 mg, 0.099 mmol), 6-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione (17.1 mg, 0.12 mmol) and triphenylphosphine (26 mg, 0.099 mmol) was dissolved in tetrahydrofuran (THF) (0.6 mL) and treated with diisopropyl diazene-1,2-dicarboxylate (DIAD) (25 uL, 0.13 mmol). The vessel was capped and stirred at 20° C. for 2 days. Additional 6-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione (17.1 mg, 0.12 mmol) and diisopropyl diazene-1,2-dicarboxylate (DIAD) (30 uL, 0.156 mmol) were added and reaction stirred for further 18 hours. The reaction was then filtered and purification attempted by mass directed autoprep (ammonium carbonate modifier), but this failed to isolate clean material. Purification successfully achieved by mass directed autoprep (formic acid modifier), to provide the required product, 1.1 mg. LCMS [LCMS1] Rt 1.13 min, m/z (ES+) 458 (M+H).

Provenance & Evidence