Day: July 14, 2021

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 3435-25-4, name is 4-Chloro-6-methylpyrimidine. A new synthetic method of this compound is introduced below., Quality Control of 4-Chloro-6-methylpyrimidine

First, into a recovery flask equipped with a reflux pipe, 5.02 g of 4,6-dichloropyrimidine, 8.29 g of phenylboronic acid, 7.19 g of sodium carbonate, 0.29 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 20 mL of water, and 20 mL of acetonitrile were put, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for one hour to be heated. Here, into the flask, 2.08 g of phenylboronic acid, 1.79 g of sodium carbonate, 0.070 g of Pd(PPh3)2Cl2, 5 mL of water, and 5 mL of acetonitrile were further put, and the reaction container was heated again by irradiation with microwaves (2.45 GHz, 100 W) for one hour. Then, water was added to this solution and an organic layer was extracted with dichloromethane. The obtained extract was washed with water and dried with magnesium sulfate. The solution which had been dried was filtered. The solvent of this solution was distilled off, and then the obtained residue was purified by silica gel column chromatography using dichloromethane as a developing solvent. As a result, a pyrimidine derivative Hdppm (yellow white powder, yield of 38%) was obtained. Note that the irradiation with microwaves was performed using a microwave synthesis system (Discover, produced by CEM Corporation).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 3435-25-4, 4-Chloro-6-methylpyrimidine.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; Takasu, Takako; Osaka, Harue; Shitagaki, Satoko; US2013/75704; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 588-36-3, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 588-36-3, name is 4-Amino-5-hydroxymethyl-2-(methylthio)pyrimidine. A new synthetic method of this compound is introduced below.

1.3 4-Amino-2-(methylthio)pyrimidine-5-carbaldehyde.; 79.5 g of active MnO2 was added over 2 minutes to a suspension of 23.8 g of alcohol obtained from the preceding step in 1600 ml of chloroform then stirred overnight at ambient temperature; the solid was filtered, washed with 3×75 ml of CHCl3 and the filtrate was concentrated under vacuum to dryness: the white solid residue was taken up in ether, filtered and dried. MP=184-186 C., m=21.05 g.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,588-36-3, 4-Amino-5-hydroxymethyl-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Sanofi-aventis; US2007/167469; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 823-89-2 ,Some common heterocyclic compound, 823-89-2, molecular formula is C4H5BrN4, 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.

General procedure: Substituted chalcones (3) (0.001 mol), 5-bromo-2-hydrazinylpyrimidine (2) (0.001 mol) and 5 drops of glacial acetic acid was ground together in a mortar using a pestle for uniform mixing. This was taken in a 50 mL beaker and subjected to microwave irradiation (90 W). The completion of the reaction was confirmed by TLC. The product obtained was poured to crushed ice, filtered, dried and recrystallized from suitable solvent mixture to give pyrazolines 4a-l.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,823-89-2, its application will become more common.

Reference:
Article; Adhikari, Adithya; Kalluraya, Balakrishna; Sujith, Kizhakke Veedu; Gouthamchandra, Kuluvar; Jairam, Ravikumar; Mahmood, Riaz; Sankolli, Ravish; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 467 – 474;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 32779-36-5, 5-Bromo-2-chloropyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

Example III-5 Morpholine (1.44 g, 16.5 mmol) is initially charged in acetonitrile (70 ml). Potassium carbonate (2.30 g, 16.5 mmol) is added, and the reaction mixture is stirred at room temperature for another hour. 5-Bromo-2-chloropyrimidine (2.90 g, 15.0 mmol) is added, and the reaction mixture is stirred at reflux for another 16 hours. After cooling, the reaction mixture is stirred into water (100 ml) and then extracted with ethyl acetate (2*50 ml). The organic phase is dried over sodium sulphate, filtered and concentrated. This gives 2.95 g (81% of theory) of 4-(5-bromo-2-pyrimidinyl)morpholine. HPLC: log P (pH 2.3)=2.15 (purity: 92%) m.p. 90 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,32779-36-5, 5-Bromo-2-chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Plant, Andrew; Seitz, Thomas; Jansen, Johannes Rudolf; Erdelen, Christoph; Turberg, Andreas; Hansen, Olaf; US2004/82586; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 611-08-5, 5-Nitrouracil, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Computed Properties of C4H3N3O4, blongs to pyrimidines compound. Computed Properties of C4H3N3O4

5-Nitrouracil (Aldrich Chemical Company) was treated with phosphorous oxychloride and NN-dimethylaniline according to the procedure described in Whittaker, J. Chem. Soc. 1951,1565, to give 2,4-dichloro-5-nitropyrimidine as an orange oil which was used without distillation immediately in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,611-08-5, 5-Nitrouracil, and friends who are interested can also refer to it.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/97162; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 5305-59-9, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 5305-59-9, name is 6-Chloropyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 6-chloropyrimidin-4-amine (0.324 g, 2.5 mmol), phenylboronic acid (0.381 g, 3.13 mmol), Na2CO3 (0.795 g, 7.50 mmol) and Bis(triphenylphosphine)palladium(II) chloride (0.035 g, 0.050 mmol) were suspended in a mixture of Dioxane (15 mL)/EtOH (2 mL)/water (3 mL). The mixture was heated a heating block at 125 C for 2 h and concentrated. The residue was purified on the silica gel using 100 % ethyl acetate, then 10% methanol in ethyl acetate. The desired fractions were concentrated to give an off-white solid (0.25 g, 58 %).1H NMR (400 MHz, DMSO-d6) d ppm 8.44 (1 H, d, J=1.26 Hz), 7.93 – 8.00 (2 H, m), 7.42 – 7.52 (3 H, m), 6.91 (2 H, s), 6.88 (1 H, d, J=1.26 Hz). LCMS (method D) tR, 2.58min., MH+ = 172.1.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 5305-59-9, 6-Chloropyrimidin-4-amine.

Reference:
Article; Iwuagwu, Christiana; King, Dalton; McDonald, Ivar M.; Cook, James; Zusi, F. Christopher; Hill, Matthew D.; Mate, Robert A.; Fang, Haiquan; Knox, Ronald; Gallagher, Lizbeth; Post-Munson Amy Easton, Debra; Miller, Regina; Benitex, Yulia; Siuciak, Judy; Lodge, Nicholas; Zaczek, Robert; Morgan, Daniel; Bristow, Linda; Macor, John E.; Olson, Richard E.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1261 – 1266;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.111196-81-7, name is 2-Chloro-5-ethylpyrimidine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.Safety of 2-Chloro-5-ethylpyrimidine

Step 1. Preparation of 4-(5-ethylpyrimidin-2-yloxy)cyclohexanol To a stirred solution of cyclohexane-1,4-diol (2.03 g, 17.5 mmol) in DMF (17 mL) was added NaH (95% wt, 177 mg, 7.01 mmol) at 0 C. The mixture was stirred for 30 min at room temperature and 2-chloro-5-ethylpyrimidine (500 mg, 3.51 mmol) was added to the mixture. After being stirred for 16 hours at 70 C., the reaction mixture was diluted with EtOAc and water. The organic layer was washed by brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=1:1) to give the desired product (520 mg, 66%) as a colorless oil. 1H NMR (400 Hz, CDCl3) delta 1.24 (3H, t, J=7.6 Hz), 1.57-1.84 (5H, m), 2.03-2.20 (3H, m), 2.57 (2H, q, J=7.6 Hz), 3.78-3.82 (1H, m), 4.94-5.01 and 5.06-5.10 (1H, each m), 8.33 (2H, s). LC-MS m/z=222.8 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,111196-81-7, 2-Chloro-5-ethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; CHEMIZON, A DIVISION OF OPTOMAGIC CO., LTD.; US2012/53180; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 6328-58-1, name is 6-Methyl-2-(methylthio)-1H-pyrimidin-4-one. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Methyl-2-(methylthio)-1H-pyrimidin-4-one

A mixture of the pyrimidone (324b; 437g), iodine (852.6g) and sodium hydroxide (134.2g) in water (2L) was heated to 80C for 15h. After cooling the reaction was neutralized with acetic acid and the solid collected to give the iodide (324c; 656g) as a light-brown solid. Used in the next step without purification.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 6328-58-1, 6-Methyl-2-(methylthio)-1H-pyrimidin-4-one.

Reference:
Patent; SCHERING CORPORATION; SOUTHERN RESEARCH INSTITUTE; ARASAPPAN, Ashok; NJOROGE, F., George; BENNETT, Frank; GIRIJAVALLABHAN, Vinay, M.; HUANG, Yuhua; HUELGAS, Regina; PIWINSKI, John, J.; SHIH, Neng-Yang; VERMA, Vishal; VELAZQUEZ, Francisco; VENKATRAMAN, Srikanth; KWONG, Cecil, D.; ANANTHAN, Subramaniam; CLARK, Jeremy; GENG, Feng; KEZAR, Hollis, S., III.; MADDRY, Joseph, A.; REYNOLDS, Robert, C.; ROYCHOWDHURY, Abhijit; SECRIST, John, A., III.; FOWLER, Anita, T.; WO2010/22121; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 355806-00-7, (3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[(methanesulfonyl) methylamino]pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid tert-butyl ester, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Recommanded Product: 355806-00-7, blongs to pyrimidines compound. Recommanded Product: 355806-00-7

Example 1; Preparation of rosuvastatin calcium salt via rosuvastatin sodium salt solution; Rosuvastatin te/f-butyl ester (60.0 g, 111.6 mmol) is dissolved in 500 mL of a 4:1 mixture of THF / water. The clear solution is warmed to 30 0C and 8.0 M NaOH (15 mL, 120.0 mmol) is added portionwise. The reaction mixture is stirred at 30 X for 2 hours giving a clear yellow solution. Then THF is removed completely under the reduced pressure (20 mbar) at 40 0C. The remaining aqueous solution is diluted with water to 500 mL and washed with AcOEt (2*200 mL). After separation from the organic layer aqueous phase is distilled under the reduced pressure (20 mbar) at 40 0C to completely remove the dissolved AcOEt. The remaining clear solution of sodium rosuvastatinate (440 mL) is diluted with water (60 mL) to 500 mL and warmed to 40 0C. To a vigorously stirring solution of sodium rosuvastatinate is added dropwise Ca(OAc)2chiH2theta (14.8 g, 84.0 mmol in 60 mL of water) over 5 minutes at 40 0C to precipitate rosuvastatin calcium. After the complete addition the suspension is stirred further for 30 minutes at 40 0C. The white precipitate is filtered off. Then a wet white solid is suspended in water (200 mL) and vigorously stirred for 1 hour at 20 0C. The undissolved precipitate is collected by filtration, washed with water (200 mL) and dried in vacuum at 40 0C to give 48.5 g (86.8 %) of rosuvastatin calcium salt as white powder (HPLC: 99.87 %).; Example 2; Rosuvastatin terf-butyl ester (60.0 g, 111.6 mmol) is dissolved in 120 mL of tetrahydrofuran (THF) and 300 ml of water treated 8.0 M NaOH (21 mL) is added portionwise. The reaction mixture is stirred at 5O0C for 2 hours. Reaction mixture is allowed to cool to room temperature and washed with 2 x 540 ml of methylcyclohexane. EPO Aqueous phase is evaporated at 600C under reduced pressure to 220 ml of total volume to eliminate organic solvents. The residue obtained is rediluted with degassed demi-water to 440 ml of total volume. To the resulting solution 1.0 g of charcoal is added and the suspension is stirred half an hour. Charcoal is filtered off. One half of the volume of the filtrate (220 ml of total 440 ml) 25.5 ml aqueous solution of calcium chloride (prepared from 10.5 ml 4M calcium chloride and 15 ml demi- water) is added during stirring on ice-bath. The suspension formed is treated vigorously with ultraturrax at cca 18000 rpm for 3 minutes. The precipitate is filtered off, suspended anew in 100 ml demi water and treated again with Ultraturax at 18000 rpm for 3 minutes on ice-bath. The product is separated by filtration, washed with 30 ml ice-cold degassed demi-water, collected from the filter and dried 12 hours at 500C in vacuum desiccator.Yield: 25.05 g of amorphous rosuvastatin calcium (99.75% area, HPLC, 0.085 % Na)The second aliquot of 220 ml of filtrate is treated on the same way except mechanical stirring instead of ultraturax mixing is performed. Yield 25.11 g (99.72% area, HPLC, 1.55 % Na); Example 3; Rosuvastatin fe/f-butyl ester (10.0 g) is dissolved in 20 mL of tetrahydrofuran and 50 ml of water treated 8.0 M NaOH (3.51 mL) is added portionwise. The reaction mixture is stirred at 500C for 1 hours. One third (26 ml of the total 78 ml) of the resulting solution is washed with 35 ml methylcyclohexane. Methylcyclohexane phase is extracted with 3 ml demi water. Combined aqueous phases are washed with 20 ml /so-propyl acetate. Aqueous phase is then concentrated by evaporation under reduced pressure at 50C to 15 – 20 ml of total volume. It is cooled on ice-bath and gradually 1.1 ml aqueous solution of 4M calcium chloride is added within a minute during stirring. It is stirred additional 30 minutes on ice-bath and the precipitated product is separated by filtration. The precipitate is washed with 4.0 ml demi water, EPO collected from the filter and dried at room temperature 12 hours in vacuum desiccator.Yield: 2.22 g of amorphous rosuvastatin calcium.Two further aliquots are washed with 20 ml ethyl acetate or 20 ml terf-butyl methyl ether respectively with similar yield and quality.; Example 4; Preparation of rosuvastatin sodium salt; Rosuvastatin fe/-butyl ester (3.0 g, 5.6 mmol) is dissolved in 25 mL of a 4:1 mixture of THF / water. The clear solution is warmed to 30 0C and 8.0 M NaOH (0.75 mL, 6.0 mmol) was added portionwise. The reaction mixture is stirred at 30 0C for 2 hours giving a clear yellow solution. Then THF is removed completely under the reduced pressure (20 mbar) at 40 0C. The remaining aqueous solution is diluted with water to 25 mL and washed with AcOEt (2×10 mL). After separation from the organic layer aqueous phase is distilled under the reduced pressure (20 mbar) at 40 0C to completely remove the dissolved AcOEt. The remaining clear solution of sodium rosuvastatinate is diluted with water to 25 mL and liophylized to afford 2.81 g (100 %) of rosuvastatin sodium salt as white powder.; Example 8; Preparation of solid rosuva…

At the same time, in my other blogs, there are other synthetic methods of this type of compound,355806-00-7, (3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[(methanesulfonyl) methylamino]pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid tert-butyl ester, and friends who are interested can also refer to it.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; WO2006/136408; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 591-55-9, 5-Aminopyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Recommanded Product: 5-Aminopyrimidine, blongs to pyrimidines compound. Recommanded Product: 5-Aminopyrimidine

To a solution of pyrimidin-5-amine (565 mg, 5.94 mmol) and diisopropylethylamine (1.046 g, 8.09 mmol) in dichloromethane (12 mL), was added a solution of ditrichloromethyl carbonate (601 mg, 2.03 mmol) in dichloromethane (6 mL). The resulting mixture was stirred at room temperature for 15 min, and 32-3 (500 mg, 1.49 mmol) and triethylamine (902 mg, 8.91 mmol, 6.00 equiv) were added sequencially. The reaction mixture was stirred at room temperature for 5 h and then the reaction was quenched by addition of methanol and then water. The reaction was extracted with dichloromethane, washed with water and brine, and dried over anhydrous sodium sulfate. After concentration, the residue was purified by silica gel column with ethyl acetate/petroleum ether (1/5) as the eluent to afford the desired product (570 mg, 84% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,591-55-9, 5-Aminopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; INVENTISBIO INC.; DAI, Xing; WANG, Yaolin; (187 pag.)WO2017/139414; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia