4-Nitrophenyl chloroformate → HCID 86586006, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6-Methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile (0.43 g, 1.7 mmol, prepared by the method described in Example 26, Step 1, in 77% yield) in THF (15 mL) at −78° C. was added LDA (1.25 mL, 2.5 mmol, 2.0 M in hexanes). The resulting mixture was stirred at −78° C. for 15 min, warmed to −25° C. for 15 min, recooled to −78° C. and 4-nitrophenyl chloroformate (0.50 g, 2.5 mmol) was added in one portion. The reaction mixture was stirred at −78° C. for 15 min, gradually warmed to room temperature, quenched with water and extracted with ethyl acetate. The organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using 50% to 70% ethyl acetate-hexane as eluant to give the title compound as a light yellow solid (0.38 g, 53%).

Provenance & Evidence