Ethyl Acetoacetate → Ethyl 2-(2-acetylaminothiazol-4-yl)-4-(2-chloro-4-fluorophenyl)-6-methyl-1,4-dihydro-pyrimidin-5-carboxylate

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Reaction Steps

2 mmol 2-Acetylamino-4-thiazolformamidine hydrochloride, 2 mmol 2-chloro-4-fluorobenzaldehyde, 2 mmol ethyl acetoacetate and 2.2 mmol sodium acetate were reacted under reflux in 10 ml anhydrous ethanol for 20 hr, concentrated, and then ethyl acetate and water were added to separate the layers. The ethyl acetate layer was dried over anhydrous sodium sulfate, and separated by a column chromatography to obtain 0.31 g of a colorless crystal with mp 220-223° C.; 1H-NMR (400 MHz, DMSO-d6) δ 1.01-1.04 (3H, m); 2.13 (3H, s); 2.40-2.42 (3H, d); 3.91-3.97 (2H, m); 5.97 (1H, s); 7.15-7.39 (3H, m); 7.64-7.83 (1H, d); 8.33-8.98 (1H, d); 12.33 (1H, s); MS (EI) 436.0 (M+).

Provenance & Evidence