Carbon Tetrachloride → Triphenylphosphine

Participants

Reaction Steps

Following the procedure described in European Patent No. 1698628, 5-benzyloxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid N′-[2-(4-fluoro-phenyl)-acetyl]-hydrazide was treated with CCl4 (7 equiv.), Ph3P (3 equiv.) and Et3N (3 equiv.) in CH3CN (10 vol) at room temperature for 1.5 h. TLC showed only one product formed. The reaction mixture was diluted with EtOAc, washed with aqueous NaHCO3 and brine, dried and concentrated to give a crude solid. For the 1.8 g scale reaction, chromatography (4 columns) plus recrystallization twice was needed to isolate the desired product without Ph3P═O contamination. NMR and MS confirmed the structure.

Provenance & Evidence