* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Example 32 2-PHENYLPYRIMIDINE-5-CARBONYL CHLORIDE A solution of ethyl 3-N,N-dimethylamino-2-formylacrylate (4.0 g, 23 mmol) (Arnold, Coll. Czech. Chem. Commun. 26:3051, 1961), benzamidine hydrochloride (4.0 g, 26 mmol) and sodium (0.65 g, 28 mmol) in EtOH (40 mL) was heated at reflux for 1 h. The solution was filtered and concentrated and the residue partitioned between EtOAc and dilute HCl (10percent). The organic layer was dried (Na2 SO4), and concentrated to give ethyl 2-phenylpyrimidine-5-carboxylate (4.0 g, 75percent yield); m.p. >220° C. (dec.).
Reference：
[1] Journal of medicinal chemistry, 2000, vol. 43, # 21, p. 3995 - 4004
[2] Patent: US5811428, 1998, A,
2
[ 80370-42-9 ]
[ 1670-14-0 ]
[ 85386-14-7 ]
Reference：
[1] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 96 - 107
3
[ 1670-14-0 ]
[ 85386-14-7 ]
Reference：
[1] Journal of Organic Chemistry, 1996, vol. 61, # 7, p. 2470 - 2483
4
[ 25023-37-4 ]
[ 1670-14-0 ]
[ 864377-28-6 ]
Yield
Reaction Conditions
Operation in experiment
58%
With potassium carbonate In ethanol; 1-ethoxyethanol at 90℃; for 24 h;
a); 5.45 g (34.8 mmol) benzamidine hydrochloride hydrate and 4.10 g (73.1 mmol) po- tassium carbonate in 50 ml ethanol are stirred at 90 °C under dry air. 20.0 g (69.7 mmol) (E)-1-(3-bromophenyl)-3-phenyl-prop-2-en-1-one in 20 ml hot ethoxy-ethanol are added slowly. After 24 h the reaction mixture is cooled to 25 °C, the product is filtered off, washed with ethanol, water and again ethanol and is used without further purification in step b) (
Stage #1: With sodium methylate In methanol; ethanol at 20℃; for 9 h; Inert atmosphere; Reflux Stage #2: With sodium hydroxide In methanol; ethanol at 70℃; for 5 h;
3-bromobenzaldehyde (18.5 g, 100 mmol), acetophenone (12.0 g, 100 mmol), 1N-sadium methoxide/methanol solution (10 ml) and ethanol (200 ml) were stirred for five hours at the room temperature under an Ar gas atmosphere. Subsequently, the reactant mixture was heated and stirred for another four hours at a reflux temperature. Next, benzamidine hydrochloride (9.4 g, 60 mmol) and sodium hydroxide (8.0 g, 200 mmol) were added thereto and stirred for five hours at 70 degrees C. After the reaction, the reactant mixture was filtered to separate an extract. The extract was refined by silica-gel column chromatography (a developing solvent: dichloromethane) to provide an intermediate body X6 as a white solid. A yield of the intermediate body X6 was 10.1 g and a yield rate thereof was 26percent.
Benzamidine hydrochloride (4.0 g, 0.25 mol) was dissolved in 64 ml of ethanol. To this 8.0 ml of a 25 wt percent solution of sodium methoxide was added. Reaction was then stirred at room temperature for 5 hrs, and filtered. Filtrate was then added to ethyl-2-cyano-4, 4-diethoxybutyrate (4.80 g, 0.21 mol). This solution was refluxed for 5 hrs.Half of solvent was removed under reduced pressure, then 80 ml of ice water was added, and the pH was adjusted to 7 with acetic acid. Material was then chilled for 6 hrs and product was isolated by vacuum filtration
With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 4h;
K2CO3 (2.1 g, 15.4 mmol) was added to a mixture of benzamidine hydrochloride hydrate (1.55 g, 10.0 mmol) and 14 (1.0 g, 7.7 mmol) in DMF at ambient temperature. The solution was heated at 100 °C for 4 h. After confirming that the reaction was complete by using TLC analysis, the solution was cooled to room temperature and water (15 mL) is added. The reaction mixture was extracted with EtOAc and brine. The organic phase was dried over Na2SO4 overnight and the solvent was removed under vacuum. The crude product was purified by silica gel column chromatography to give the target product 2g. 1H NMR (600 MHz, DMSO-d6) delta 9.31 (s, 2H), 8.49-8.44 (m, 2H), 7.59 (ddd, J = 15.9, 7.7, 3.6 Hz, 3H), 4.40 (q, J = 7.1 Hz, 2H), 1.37 (t, J = 7.1 Hz, 3H).
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