2-Bromoethanol → HCID 10270925, compound

Participants

Reaction Steps

0.180 g (0.540 mmol) of the 6-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2-methyl-5-nitro-3H-pyrimidin-4-one (example 1) and 0.142 g (1.1 mmol) of N-ethyldiisopropylamine, dissolved in 5.0 ml of N,N-dimethylformamide, were slowly added between −5° C. and 0° C. to a suspension of 0.923 g (7.0 mmol) of 2-bromo-ethanol and 0.897 g (6.5 mmol) of potassium carbonate in 5.0 ml of N,N-dimethylformamide. The reaction mixture was then stirred at room temperature for 48 hours. It was then poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of dichloromethane. The combined dichloromethane phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 9:1 to 1:1 v/v gradient of hexane and ethylacetate as the eluent giving 0.039 g (0.10 mmol, 19.1% of theory) of the 2-{6-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2-methyl-5-nitro-pyrimidin-4-yloxy}-ethanol as a light yellow amorphous solid; MS: [M+H]+=378; and 0.091 g (0.241 mmol, 44.7% of theory) of the 6-[4-(4-fluoro-phenyl)-piperazin-1-yl]-3-(2-hydroxy-ethyl)-2-methyl-5-nitro-3H-pyrimidin-4-one as yellowish amorphous solid; MS: [M+H]+378.

Provenance & Evidence