Triethylamine → 5-Chloro-1-[(4-methylphenoxy)methyl]pyrimidin-2(1H)-one

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Reaction Steps

The title compound was prepared by adding a solution of 4-(chloromethoxy)toluene (see J.Appl. Chem. 3, 266(1953)) (10 mmol) in dichloromethane (10 ml) to a solution of 5-chloropyrimidin-2-one hydrochloride (10 mmol) and triethylamine (20 mmol) in dichloromethane (50 ml). The mixture was stirred at room temperature for 2 days. The product, 1.90 g (76%), consisted of the N- and O-isomers in the ratio 3:1. The N-isomer was isolated by its lower solubility in ether; m.p. 186° C. (acetone). (Found: C57.59; H4.65 Calc. for C12H11ClN2O2 : C57.49; H4.43) 1H NMR (CDCl3): δ 2.25 (Me), 5.74 (CH2), 6.8-7.3 (Ph), 7.80 and 8.50 (H-4 and H-6, respectively, J 3 Hz). IR (KBr): 1680 cm-1 (CO). MS [70 eV, m/z% rel. int.)[: 250 (7,M), 145 (31), 143 (100), 116 (28).

Provenance & Evidence