Synthetic Route of 287714-35-6 ,Some common heterocyclic compound, 287714-35-6, molecular formula is C6H5ClN2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
2-Chloropyrimidine-5-carboxylic acid methyl ester (434mg, 2.33 mmol) was added to a stirring suspension of (2R)-2-amino-3-methyl-3-{[(2E)-3,7,11,15- tetramethylhexadec-2-en-1-yljsulfanyl}butanoic acid (ig, 2.33 mmol) and N,Ndiisopropylethylamine (1.2lmL, 6.99 mmol) in dioxane (lOmL) at room temperature and heated to 60C overnight. The reaction mixture is cooled to room temperature and washed once with brine. The reaction mixture is diluted with an additional 5mL of dioxane, followed by addition of 1M lithium hydroxide (lOmL) at room temperature and stirred overnight. The reaction mixture is diluted with ethyl acetate, washed with 10% w/v citric acid solution, then brine and dried over magnesium sulfate. The ethyl acetate is filtered and concentrated on a rotary evaporator to give the crude product as a yellow oil that is purified by flash chromatography using ethyl acetate in hexanes as the eluent to give the purified carboxylic acid as an off-white solid. The carboxylic acid was dissolved in ethanol, then solid sodium ethoxide was added until the pH reached 9. The resulting ethanolic suspension was centrifuged at 2000 rpm for 2 minutes. The ethanol was decanted and the ethanol wash was repeated twice more. Acetonitrile was then substituted for ethanol and the wash was repeated three times. The resulting solid was dried on a rotary evaporator to give 165mg of a white solid in 12% yield. ?H NMR (500 MHz, Deuterium Oxide) 8.61 (s, 2H), 5.07 (s, 1H), 4.21 (s, 1H), 3.17 – 3.02 (m, 2H), 1.92 – 1.74 (m, 2H), 1.49 (d, J = 6.4 Hz, 3H), 1.44 – 0.82 (m, 26H), 0.79 – 0.64 (m, 12H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,287714-35-6, its application will become more common.
Reference:
Patent; SIGNUM BIOSCIENCES, INC.; VORONKOV, Michael; PEREZ, Edwardo; HEALY, Jason; FERNANDEZ, Jose; (139 pag.)WO2018/132759; (2018); A1;,
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