ETHYL 6-OXO-2-PHENYL-1,6-DIHYDRO-5-PYRIMIDINECARBOXYLATE synthesis
- Product Name:ETHYL 6-OXO-2-PHENYL-1,6-DIHYDRO-5-PYRIMIDINECARBOXYLATE
- CAS Number:55613-22-4
- Molecular formula:C13H12N2O3
- Molecular Weight:244.25
1670-14-0
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87-13-8
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55613-22-4
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Yield:55613-22-4 75%
Reaction Conditions:
Stage #1: benzamidine monohydrochloridewith sodium ethanolate in ethanol at 20; for 0.5 h;
Stage #2: diethyl 2-ethoxymethylenemalonate in ethanol at 20 - 80;
Steps:
Ethyl 6-oxo-2-phenyl-1,6-dihydropyrimidine-5-carboxylate (7).
Sodium (3 g, 131 mmol) was dissolved in abs. ethanol (48 mL) to obtain 21% solution of sodium ethoxide. Benzamidine hydrochloride (11.1 g, 70.7 mmol) was added to the mixture at room temperature and the mixture was stirred for 30 min. An ethanol (25 mL) solution of 2-ethoxy-methylene malonate (13.9 g, 64.3 mmol) was added dropwise to the reaction mixture, and while stirring, the clear mixture slowly turn to orange turbid liquid. Next, the reaction was raised to 80 oC to reflux for 6 hours and then cooled to room temperature. The mixture was added 6M HCl solution with stirring until pH to 4, and the precipitated solid was suction filtered, washed with water, and then dried to give the compound 7 as a pale pink solid 11.78g (yield 75%); 1H NMR (300 MHz, CDCl3) δ (ppm): 8.99 (s, 1H), 8.36-8.39 (m, 2H), 7.51-7.63 (m, 3H), 4.46 (q, J = 7.1 Hz, 2H), 1.44 (t, J = 7.1 Hz, 3H)
References:
Lee, Jihye;Jung, Jae Ho;Lee, Byung Chul;Lee, Sang-Yoon [Bulletin of the Korean Chemical Society,2016,vol. 37,# 11,p. 1874 - 1877] Location in patent:supporting information
38026-46-9
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55613-22-4
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$38.00/500mg
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55613-22-4
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$38.00/500mg