Pyrimidines

Synthetic Route of 183438-24-6, 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.183438-24-6, name is 5-Bromo-2-iodopyrimidine, molecular formula is C4H2BrIN2, molecular weight is 284.88, as common compound, the synthetic route is as follows.

A mixture consisting of 5-bromo-2-iodopyrimidine (Bridge Organics, 10.0 g, 35.1 mmol), benzene boronic acid (Alfa Aesar, 4.25 g, 35.1 mmol), tetrakis(triphenylphosphine)palladium (Strem, 0.405 g, 0.351 mmol), toluene (150 mL), and a 2 M aqueous sodium carbonate solution (35 mL) was stirred at 115 C. (degrees Celsius) under a nitrogen atmosphere for 16 hours. After cooling to room temperature, the mixture was partitioned between chloroform (250 mL) and brine (200 mL). The phases were separated and the organic phase was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an orange oil (9.1 g). The crude product was purified by flash silica column chromatography. Elution through a 500-g Analogix flash silica cartridge with 100% hexanes afforded the title intermediate as a white solid (3.15 g, 38% yield). Rf 0.69 with 9:1 v/v hexanes-ethyl acetate; 1H-NMR (400 MHz; CDCl3) delta 8.83 (s, 2H), 8.44-8.38 (m, 2H), 7.52-7.46 (m, 3H); MS (APCI+) m/z 236.9 (M+1).

The chemical industry reduces the impact on the environment during synthesis 183438-24-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CAYMAN CHEMICAL COMPANY; US2010/75990; (2010); A1;,
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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 148550-51-0, name is Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

General procedure: 60percent Sodium hydride (w/w) in mineral oil (0.0015 mol) was added to a mixture of appropriate III (0.001 mol) in THF (15 ml) under the condition of inert atmosphere using N2 flow at 5°C. The reaction mixture was kept for 1 h at room temperature. A solution of 2-(methylsulfonyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.0015 mol) in THF (15 ml) was slowly added to reaction mixture. The resulting reaction mixture was stirred for 2-3 h at 5°C. The distilled water (20 ml) was added. The reaction mixture was extracted (10 ml x 3) with dichloromethane. The separated organic layer was dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure to obtain crude product, recrytallized by ethyl acetate.

With the rapid development of chemical substances, we look forward to future research findings about 148550-51-0.

Reference:
Article; Rajak, Harish; Agarawal, Avantika; Parmar, Poonam; Thakur, Bhupendra Singh; Veerasamy, Ravichandran; Sharma, Prabodh Chander; Kharya, Murli Dhar; Bioorganic and Medicinal Chemistry Letters; vol. 21; 19; (2011); p. 5735 – 5738;,
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Adding a certain compound to certain chemical reactions, such as: 4318-56-3, 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione, 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 C5H5ClN2O2, blongs to pyrimidines compound. Computed Properties of C5H5ClN2O2

General procedure: 6-Chloropyrimidine-2,4(1H, 3H)-dione derivatives 1 (1.0 mmol) and N-hydroxyformimidoyl chloride derivatives 2 (1.2 mmol) were combined and dissolved in methanol (15mL), followed by the addition of triethylamine (3.0 mmol). Subsequently, the reaction mixture was stirred in a round-bottom flask (25mL) at room temperature for 5h. After completion of the reaction as indicated by TLC, the mixture was evaporated by rotary evaporator, extracted with ethyl acetate, dried over Na2SO4, then concentrated and purified by flash column chromatography (PE/EA=5:1) to yield compounds 3a-t.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4318-56-3, 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Article; Jiang, Kun-Ming; Jin, Yi; Lin, Jun; Tetrahedron; vol. 73; 47; (2017); p. 6662 – 6668;,
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Application of 270912-79-3, 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. 270912-79-3, name is 2-((5-Bromopyrimidin-2-yl)oxy)acetic acid. A new synthetic method of this compound is introduced below.

Solid 3,4-methoxyphenylboronic acid (1.22 g, 6.72 mmol, 1.05 equiv) was added to a solution of (5-bromopyrimidin-2-yloxy)acetic acid 3e (1.5 g, 6.4 mmol) in 1-propanol (50 mL). The suspension was stirred until all ingredients had dissolved. The resulting solution was treated with Pd(OAc)2 (29 mg, 0.13 mmol, 0.02 equiv), PPh3 (103 mg, 0.39 mmol, 0.06 equiv), 2M Na2CO3 (12 mL, 24 mmol, 3.8 equiv), and deionized water (10 mL). The mixture was heated at reflux under N2 for 1 h. Additional water (20 mL) was added and the N2 inlet removed. After cooling to rt, the solution was acidified with 4M HCl. The resulting precipitate was filtered, washed with cold diluted HCl, and dried under vacuum to give 5-(3,4-dimethoxyphenyl)-pyrimidin-2-yloxy)acetic acid 3f as a brown solid (1.30 g, 70%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,270912-79-3, 2-((5-Bromopyrimidin-2-yl)oxy)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; Du Bois, Daisy Joe; Mao, Long; Rogers, Daniel Harry; Williams, John Patrick; US2004/14775; (2004); A1;,
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Electric Literature of 90905-32-1, 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 90905-32-1, name is 2-Methoxypyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Under ice-cooling, 3.0 mol/L methyl magnesium bromide/diethyl ether (0.7 mL) was added to a solution of2-methoxypyrimidine-5-carbaldehyde (138 mg) in tetrahydrofuran (5 mL), followed by stirring for 1 hour.Acetic acid was added thereto, and the solvent was distilled off under reduced pressure. The obtainedresidues were purified by silica gel column chromatography (hexane:ethyl acetate=1:1), whereby 1-(2-methoxypyrimidin-5-yl)ethanol (126 mg) was obtained.(1853)MS(ESI m/z): 155 (M+H)(1854)RT(min): 0.52

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 90905-32-1, 2-Methoxypyrimidine-5-carbaldehyde.

Reference:
Patent; FUJIFILM Corporation; KUBO, Yohei; ANDO, Makoto; TANAKA, Hidehiko; OSAKA, Shuhei; MATSUMOTO, Takuya; NAKATA, Hiyoku; TERADA, Daisuke; NITABARU, Tatsuya; (379 pag.)US2016/168139; (2016); A1;,
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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. 56-09-7, name is 2-Amino-6-hydroxypyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Amino-6-hydroxypyrimidin-4(3H)-one

General procedure: Typically, 2-aminopyrimidine-4,6-diol (1a, 0.5 mmol, 1.0 equiv)/2-methylpyrimidine-4,6-diol (1b, 0.5 mmol, 1.0 equiv), nitroolefins (2, 0.5 mmol, 1.0 equiv), as well as water (2.5 mL) were introduced into a 10 mL reaction vial. Then, the reaction vial was closed and stirred for given time at 90 C. Upon completion, the reaction mixture was cooled to room temperature and diluted with cold water (30 mL). The solid product was collected by filtration and was purified by recrystallization from hot 95% EtOH to afford the goal product 5-arylfuro[2,3-d]pyrimidin-4-ol (3) as off-white to yellow solid.

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, 56-09-7, 2-Amino-6-hydroxypyrimidin-4(3H)-one.

Reference:
Article; Li, Chunmei; Zhang, Furen; Tetrahedron Letters; vol. 58; 16; (2017); p. 1572 – 1575;,
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Application of 39876-88-5, Adding some certain compound to certain chemical reactions, such as: 39876-88-5, name is 4-Chlorobenzofuro[3,2-d]pyrimidine,molecular formula is C10H5ClN2O, 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 39876-88-5.

In a pressure vessel equipped with a magnetic stirring bar was added (4-bromo-2,6-difluorophenyl)methanamine.HC1 (1 g, 3.87 mmol), and 4-chlorobenzofuro[3,2-djpyrimidine (0.792 g, 3.87 mmol) in acetonitrile (20 mL). Hunig?s base (2.70 mL, 15.47 mmol) was added and the mixture was heated to 80 C in a preheated oil bath and allowed to stir for 48 hours overnight. Cool to RT and filter formed solids, wash with excess acetonitrile, filter and dry under vacuum to give 863 mg (5 7%) of N-(4-bromo-2,6-difluorobenzyl)benzofuro[3,2-djpyrimidin-4-amine as a fluffy white solid. LCMS (M+1) = 389.6 and 391.6.

According to the analysis of related databases, 39876-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
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Application of 33034-67-2, 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 33034-67-2 as follows.

Step 11: A mixture of (R)-methyl l-isopropyl-7-(methylsulfonyl)-l,2,3,4- tetrahydrobenzo[4,5]imidazo[l,2-a]pyrazine-8-carboxylate (0.9 g, 2.56 mmol), 2-chloro-4- (trifluoromethyl)pyrimidine (1.0 g, 5.1 mmol, 2 eq.) and DIEA (1.0 g, 7.7 mmol, 3 eq.) in i- PrOH (6 mL) was stirred in a microvave oven at 150 °C for 2 h. TLC showed the starting material was consumed completely (PE : EtOAc = 3 : 1). The solvent was removed in vacuo at 40 °C, and the residue was purified by column chromatography on silica gel eluting with PE / EtOAc = 6 / 1 to give (R)-methyl l-isopropyl-7-(methylsulfonyl)-2-(4- (trifluoromethyl)pyrimidin-2-yl)-l,2,3,4-tetrahydrobenzo[4,5]imidazo[l,2-a]pyrazine-8- carboxylate (1.0 g, 78percent yield) as a white solid.LC-MS m/z 498.1 [M+H]+. 1H NMR (CDC13 300MHz): delta 8.52 (d, 7 = 4.8 Hz, 1H), 8.13 (s, 1H), 8.06 (s, 1H), 6.83 (d, 7 = 4.8 Hz, 1H), 6.06 (d, 7 = 7.8 Etazeta,IotaEta), 5.39-5.28 (m, 1H), 4.33-4.24 (m, 1H), 4.20-4.12 (m, 1H), 3.93 (s, 3H), 3.77-3.65 (m, 1H), 3.39 (s, 3H), 2.52-2.38 (m, 1H), 1.25 (d, 7 = 6.9 Hz, 3H), 1.02 (d, 7 = 6.6 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33034-67-2, its application will become more common.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; DONG, Chengguo; FAN, Yi; LEFTHERIS, Katerina; LOTESTA, Stephen; SINGH, Suresh, B.; TICE, Colin; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2013/138565; (2013); A1;,
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Synthetic Route of 63931-21-5, 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.63931-21-5, name is 5-Bromo-2,4,6-trichloropyrimidine, molecular formula is C4BrCl3N2, molecular weight is 262.3192, as common compound, the synthetic route is as follows.

5-Bromo-2,4,6-trichloropyrimidine (1.28 g, 4.88 mmol) and 3,3-difluorocyclobutan- amine hydrochloride (715 mg, 4.98 mmol) were suspended in acetonitrile (6 mL) and N,N- diisopropylethylamine (1.55 g, 2.1 mL, 12 mmol) was added at room temperature. The resulting yellow solution was stirred for 7 h at room temperature. After that, the reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (silica gel, 80 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 10:90) to yield, after drying in vacuo (40C, 5 mbar), the title compound as a pale yellow oil (1.188 g, 73%). HPLC (method (0254) LCMS_fastgradient) tR = 1.31 min. 1H NMR (CDC13, 300 MHz): delta 2.48-2.67 (m, 2 H), 3.08-3.25 (m, 2 H), 4.39-4.53 (m, 1 H), 5.78-5.90 (m, 1 H). MS (ES+) m/z 330.0, 332.0, 334.0 [M+H, Br & 2 CI isotopes] .

Statistics shows that 63931-21-5 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2,4,6-trichloropyrimidine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; JAKOB-ROETNE, Roland; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; STEINER, Sandra; (89 pag.)WO2018/11164; (2018); A1;,
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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. 3921-01-5, name is 2,4-Dibromopyrimidine, molecular formula is C4H2Br2N2, 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. Quality Control of 2,4-Dibromopyrimidine

2,4-dibromopyrimidine (438.4mg, 1.84mmol) and potassium carbonate (1.27g, 9.21mmol) in tetrahydrofuran (10mL) were added together and stirred at room temperature for 5min. Morpholine (174.8muL, 2.03mmol) was then added dropwise and the solution continued to stir at room temperature for 5h. The reaction mixture was filtered and the filtrate was collected and then concentrated under reduced pressure. The products were purified by silica column chromatography in hexanes and ethyl acetate to afford 28a and 28b in 19% and 66% yields, respectively. (0070) 4-(4-bromopyrimidin-2-yl)morpholine (28a). (White solid, Yield: 19%). 1H NMR (500MHz, CDCl3) delta ppm 3.74-3.77 (m, 4H) 3.79-3.83 (m, 4H) 6.70 (d, J=4.88Hz, 1H) 8.05 (d, J=4.88Hz, 1H). LCMS found 246.0, [M+H]+. (0071) 4-(2-bromopyrimidin-4-yl)morpholine (28b). (White solid, Yield: 66%) 1H NMR (500MHz, CDCl3) delta ppm 3.66 (br. s., 4H) 3.76-3.83 (m, 4H) 6.43 (d, J=6.35Hz, 1H) 8.02 (d, J=6.35Hz, 1H). LCMS found 246.0, [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 3921-01-5.

Reference:
Article; Woodring, Jennifer L.; Bachovchin, Kelly A.; Brady, Kimberly G.; Gallerstein, Mitchell F.; Erath, Jessey; Tanghe, Scott; Leed, Susan E.; Rodriguez, Ana; Mensa-Wilmot, Kojo; Sciotti, Richard J.; Pollastri, Michael P.; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 446 – 459;,
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