Triethylamine → 1-(4-Chlorophenoxy)methyl-5-trifluoromethylpyrimidin-2-one

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Reaction Steps

A solution of 1-chloromethoxy-4-chloro-benzene [see Preparation 11] (0.35 mmol) in dichloromethane (1 ml) was added with stirring at room temperature to a solution prepared from 5-trifluoromethyl-pyrimidin-2-one (0.33 mmol) and triethylamine (0.33 mmol) in dichloromethane (5 ml). The mixture was stirred at room temperature for 24 h and then it was stirred at 70° C. for 30 min, the solvent was then distilled off, the residue triturated with water, the residual material extracted with chloroform and the dried (MgSO4) chloroform solution evaporated to yield the product, 60 mg (62%), as a mixture of the N- and O-isomers in the ratio 5:1. The isomers were separated by their different solubilities in ether, the O-isomer being the more soluble. The title compound, the N-isomer had m.p. 98° C. (Found C46.78; H2.88. Calc. for C12H8ClF3N2O3 : C47.30; H2.65)1H NMR (CDCl3): δ 5.85 (CH2), 6.8-7.4 (Ph), 8.15 (H-4, J4.6 3 Hz) 8.76 (H-6) MS [70 eV; m/z (% rel. int.)]; 177 (100), 150(10), 75(5), IR (KBr); 1690cm-1 (CO).

Provenance & Evidence