Nitrogen → 3-(3-fluoro-4-thiomorpholinophenyl)-2,6-dimethylpyrimidin-4(3H)-one

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Reaction Steps

To a solution of 3-fluoro-4-thiomorpholinoaniline (1.20 g, 5.65 mmol) in anhydrous CH2Cl2 (60 mL) was added trimethylaluminium (28.5 mL, 28.5 mmol, 1 M in heptane) carefully dropwise under the protection of N2. Upon the end of addition the mixture was stirred at rt for 40 min, followed by the addition of a solution of methyl 3-acetaminocrotonate (2.66 g, 16.92 mmol) in anhydrous CH2Cl2 (20 mL). Upon the end of addition the reaction mixture was stirred at rt for another 6 h, then quenched with water and extracted with CH2Cl2. The combined organic phases were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as pale yellow solid (0.91 g, 67%). The compound was characterized by the following spectroscopic data:

Provenance & Evidence