Reaction of 2-(2-oxo-2-arylethylidene)-2,3-dihydropyrimidine-4(1H)-ones with aldehydes

Specific Features of Tosylation of 2-Substituted Pyrimidin-4(3H)-ones Containing a Double Bond in the α-Position of the Side Chain

“…The reaction progress and the purity of the synthesized compounds were monitored by TLC on Silufol UV-254-VIS plates; eluent chloroform-hexane, 5 : 1 (3a, 3b, 4a, 4b, 5, 10, and 12) or methanol-acetonitrile-chloroform, The starting compounds were synthesized by the following procedures: 1 [10], 2 [2], 7, 8 [11], and 9 [12].…”

“…1 H NMR spectrum (CDCl 3 ), δ, ppm: 2.35 s (3H, CH 3 ), 2.41 s (3H, CH 3 ), 6.31 d.d (1H furan , J 3.1, 1.5 Hz), 6.51 d (1H furan , J 3.1 Hz), 6.65 s (1H pyrimidine ), 7.24 d (1H furan , J 1.5 Hz), 7.30 d (2H arom , J 8.1 Hz), 7.37 t (2H arom , J 7.5 Hz), 7.49 t (1H arom , J 7.5 Hz), 7.78 s (1H olefi n ), 7.82 d (2H arom , J 8.1 Hz), 7.92 d (2H arom , J 7.5 Hz). 13 (11). Freshly distilled triethylamine, 0.1 mL, was added to a mixture of 0.26 g (1 mmol) of compound 1 and 0.2 g (1 mmol) of toluenesulfonyl chloride in 20 mL of anhydrous THF, and the reaction mixture was left for 30 days in closed vessel at room temperature.…”