Sodium Carbonate → 2-Methyl-5-nitro-4-(4-phenyl-piperidin-1-yl)-6-(2,2,2-trifluoro-ethoxy)-pyrimidine

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Reaction Steps

0.591 g (2.55 mmol) of 2,2,2-trifluoroethyl trifluoromethanesulfonate were added slowly at room temperature to a suspension of 0.200 g (0.636 mmol) of the 2-methyl-5-nitro-6-(4-phenyl-piperidin-1-yl)-3H-pyrimidin-4-one (example 5) and 0.135 g (1.27 mmol) of sodium carbonate in 5.0 ml of acetone. After stirring of the reaction mixture for 2 hours, 0.136 g (0.99 mmol) of potassium carbonate were added and stirring continued for 18 hours. Additional 0.296 g (1.27 mmol) of 2,2,2-trifluoroethyl trifluoromethanesulfonate were added and stirring continued for 4 hours. The reaction mixture 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 0.077 g (0.194 mmol, 30.5% of theory) of the 2-methyl-5-nitro-4-(4-phenyl-piperidin-1-yl)-6-(2,2,2-trifluoro-ethoxy)-pyrimidine as a light yellow solid; m.p. 114-117° C.; MS: [M+H]+=397; and 0.166 g (0.419 mmol, 65.8% of theory) of the 2-methyl-5-nitro-6-(4-phenyl-piperidin-1-yl)-3-(2,2,2-trifluoro-ethyl)-3H-pyrimidin-4-one as yellowish solid;

Provenance & Evidence