Pyrimidines

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

Related Products of 4595-60-2, 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 4595-60-2, name is 2-Bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Step 3: 2-(6-Bromopyridin-2-yl)pyrimidine Under argon, 54.5 ml (137.1 mmol) of a 2.5-molar solution of n-butyllithium (n-Buli) were diluted with 70 ml of THF. At a temperature of less than -70 C., 32.5 g (137.1 mmol) of 2,6-dibromopyridine, dissolved in 150 ml of THF, were added dropwise. The mixture was stirred for 15 min and, still at a temperature of less than -70 C., 9.2 ml (107 mmol) of a 5.6-molar solution of zinc chloride in diethyl ether were then added. The mixture was allowed to thaw, and a solution of 17.4 g (109 mmol) of bromopyrimidine in 50 ml of THF and a suspension of 3.9 g (3.4 mmol) of tetrakis(triphenylphosphine)palladium in 50 ml of THF were added. The mixture was boiled under reflux for 4 h, and after cooling Na-EDTA in water and dilute aqueous sodium hydroxide solution to pH=10 were added. The mixture was filtered off with suction to remove undissolved particles, the aqueous phase was extracted three times with ethyl acetate, the combined organic phases were dried with MgSO4 and the mixture was concentrated by evaporation.

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 4595-60-2, 2-Bromopyrimidine.

Reference:
Patent; Bayer CropScience AG; US2011/166143; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 16357-69-0, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 16357-69-0 as follows.

Example 47A N-(5-Cyanopyrimidin-4-yl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamide At RT, 39.4 g (145 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (preparation described in US2010/004235, page 27) were initially charged, and then thionyl chloride (370 ml) was added. The suspension was heated to reflux for 2 h and the now clear solution was concentrated under reduced pressure. 100 mg (0.345 mmol) of the acid chloride thus prepared were initially charged in pyridine (1.0 ml) and then 41.5 mg (0.345 mmol) of 4-amino-5-cyanopyrimidine were added in portions. The mixture was stirred at RT for 7 h and then left to stand overnight. Subsequently, volatile constituents were removed under high vacuum, the residue was separated by means of preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid gradient) and the product fractions were concentrated. This gave 30 mg (23% of theory) of the title compound in solid form. LC-MS (method 1): Rt=2.06 min MS (ESIpos): m/z=374 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=5.91 (s, 2H), 7.14-7.20 (m, 1H), 7.22-7.33 (m, 2H), 7.35-7.42 (m, 1H), 7.49-7.54 (m, 1H), 8.57-8.62 (m, 1H), 8.73-8.77 (m, 1H), 9.28 (d, 2H), 11.64 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16357-69-0, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Follmann, Markus; Stasch, Johannes-Peter; Redlich, Gorden; Ackerstaff, Jens; Griebenow, Nils; Knorr, Andreas; Wunder, Frank; Li, Volkhart Min-Jian; Baerfacker, Lars; Weigand, Stefan; US2014/148433; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 591-55-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of X-Phos (0.04 equiv) and Pd2(dba)3 (0.02 equiv) in toluene (15 vol) was bubbled with nitrogen and heated to 60 C for 15 min. (2S,4R)-1-(2-(3-acetyl-5-bromo-1H-indol-1-yl)acetyl)-4-fluoro-N-(4-phenylbutyl)pyrrolidine-2-carboxamide (1 equiv), 5- aniinopyriniidine (1.2 equiv) and sodium tert-butoxide (1.4 equiv) was added to the reaction mixture and the reaction mixture was heated to 100 C for 16 h. After completion of the reaction, the reaction mixture was quenched with water. The resulting mixture was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous Na2S04, filtered and then concentrated. The residue was purified by column chromatography on silica gel using DCM/MeOH to give (2S,4R)-1-(2-(3-acetyl-5-(pyrimidin-5-ylamino)-1H-indol-1-yl)acetyl)-4-fluoro-N-(4-phenylbutyl)pyrrolidine-2-carboxamide. H NMR (400 MHz, DMSO-d6) delta 8.57 (s, 1H), 8.48 – 8.45 (m, 3H), 8.22 (s, 1H), 8.02 – 8.00 (m, 2H), 7.43 (d, J = 8.8 Hz, 1H), 7.19 – 7.05 (m, 5H), 5.56 – 5.32 (m, 2H), 5.15 (d, J= 17.1 Hz, 1H), 4.38 – 4.34 (m, 1H), 4.16 – 4.11 (m, 1H), 3.95 – 3.83 (m, 1H), 3.07 – 2.99 (m, 4H), 2.40 (s, 3H), 2.38 – 2.34 (m, 1H), 2.01 – 1.98 (m, 1H), 1.56 – 1.48 (m, 2H), 1.41 – 1.33 (m, 2H).

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 591-55-9, 5-Aminopyrimidine.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (319 pag.)WO2017/35351; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 18740-38-0, name is Thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H4N2O2S

Under a nitrogen streamThieno [2,3-d] pyrimidine-2,4 (1H, 3H) -dione (8.4 g, 50.0 mmol) and phosphoryl chlorideL), which was stirred for 3 hours at 106 C. After completion of the reaction, the organic layer was separated using ethyl acetateWater was removed using MgSO4. The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound2,4-dichlorothieno [2,3-d] pyrimidine (4.2 g, 20.5 mmol, yield 41%).

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, 18740-38-0, Thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; Doosan Corporation; Kim, Hong Suk; Sim, Jae Uii; Kim, Tae Hyung; Lee, In Hyuk; La, Jong Gyu; Kim, Uhn Jin; Baek, Young Mi; (56 pag.)KR2015/36982; (2015); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 56686-16-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 56686-16-9 as follows.

General procedure: To a stirred anhydrous THF containing 5-bromo-2,4-dimethoxypyrimidine (0.29g, 1.3mmol) was added dropwise a 2.5M n-BuLi/hexane solution (0.6mL, 1.4mmol) at 195K under argon atmosphere. After 30min, 8a (0.52g, 1.3mmol) was added and the reaction mixture was stirred for 2h at this temperature. The reaction was allowed to warm to room temperature and quenched by addition of water. The product was extracted with diethyl ether. Then the combined organic layers were dried over MgSO4, filtered and concentrated. Column chromatography on SiO2 with petroleum ether and ethyl acetate (v/v=6/1) as the eluent afforded 0.35g of 1o as a colorless solid in 52% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56686-16-9, its application will become more common.

Reference:
Article; Liu, Hongliang; Pu, Shouzhi; Liu, Gang; Chen, Bing; Dyes and Pigments; vol. 102; (2014); p. 159 – 168;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia