Pyrimidines

Electric Literature of 1197953-49-3, Adding some certain compound to certain chemical reactions, such as: 1197953-49-3, name is (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide,molecular formula is C12H12Cl2N3OP, 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 1197953-49-3.

The above compound B (0.1g, 0.53mmol) and 4-(ortho dimethyl phosphinyl anilino)- 5- chloro – 2-chloro pyrimidine (0.17g, 0.53mmol) were dissolved in a mixture of 2-butanol (1.2mL) & trifluoroacetic acid (0.25 mL) and were heated to 100 C in a seal tube for overnight. The reaction mixture was then cooled to rt and poured into a saturated NaHCC solution while stirring to afford an orange solid which was filtered, washed with Et.20 to remove final traces of water. The product was dried to afford C (0.19g) which was directly used in the next step.

According to the analysis of related databases, 1197953-49-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; ZHU, Xiaotian; WANG, Yihan; SHAKESPEARE, William, C.; HUANG, Wei-Sheng; DALGARNO, David, C.; WO2013/169401; (2013); A1;,
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Electric Literature of 2915-16-4, 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 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Then , Under nitrogen flow at room temperature,the mixture4.08g of 9-phenyl-9H, 9’H-3,3′-dicarbazole, 2.93g of 2-chloro-4,6-diphenylpyrimidine,1.35g of Sodium tert-butoxide, 100ml of Dehydrated o-xylene were stirred. Tothe mixed solution was added 0.27 g of Tris(dibenzylideneacetone)dipalladium(0),0.16g of Tri-tert-butyl-tetrafluoroborate then heated at at 140 C and stirred for 1 hour. Carried out evaporation after the mixedsolution was directly filtered. Added200ml of methanol, refluxed for 2h and carried out filtration. The resultingsolid was purified by column chromatography on silica gel and dried in vacuo togive 5.7 g of a pale yellow powder.

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 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine.

Reference:
Patent; TORAY INDUSTRIES, INC.; NAGAO, KAZUMASA; TOMINAGA, TSUYOSHI; KWON, JINWOO; (86 pag.)TWI523840; (2016); B;,
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Adding a certain compound to certain chemical reactions, such as: 26032-72-4, 2,4-Dichloro-6-phenylpyrimidine, 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, COA of Formula: C10H6Cl2N2, blongs to pyrimidines compound. COA of Formula: C10H6Cl2N2

4.5 g of 4-phenyl-2,6-dichloropyrimidine (20 mmol, 2 eq), 3.77 g of ((4-(12H-benzofuro[2,3-a]carbazol-12-yl)phenyl)boronicacid) 10mmol, 1eq) 2M potassium carbonate solution: toluene: ethanol = 1:2:1 (volume ratio, total 80ml), N2 extraction three times to ensure an oxygen-free environment,0.116 g of tetrakistriphenylphosphine palladium (0.1 mmol, 1% eq) was added under the protection of N2.N2 was pumped out three times to ensure an oxygen-free environment, and the temperature was raised to 90 C under the protection of a continuous N2 flow to maintain the reaction.After completion of the reaction, toluene and ethanol were distilled off under reduced pressure.Aqueous phase was extracted with dichloromethane to give organic phase was dried over anhydrous magnesium sulfate, mixed with silica gel sample was added, was subjected to column chromatography to give the product 3.9g (75%);

At the same time, in my other blogs, there are other synthetic methods of this type of compound,26032-72-4, 2,4-Dichloro-6-phenylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Huazhong University of Science and Technology; Wang Lei; Zhang Qing; Zhuang Shaoqing; (40 pag.)CN108285452; (2018); A;,
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Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine, the common compound, a new synthetic route is introduced below. Product Details of 49844-90-8

Indole I (400.88g) in 25OmL THF, 2L of IN K1BuO, and 381g pyrimidine II in 35OmL THF were combined with cooling to maintain under 40 0C and allowed to stir at r.t, for 1 hour. The solvent was then removed in vacuo and the solid was suspended in MeOH, filtered, washed with MeOH, water, and again with MeOH, to yield 87.56% III.

The synthetic route of 49844-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2009/138340; (2009); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 62802-42-0, Adding some certain compound to certain chemical reactions, such as: 62802-42-0, name is 2-Chloro-5-fluoropyrimidine,molecular formula is C4H2ClFN2, 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 62802-42-0.

Preparation 123 N-[(4aR,7aR)-6-(5-Fluoropyrimidin-2-yl)-7a-(2-thienyl)-4,4-a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide A solution of N-[(4aR,7aR)-7a-(2-thienyl)-4-a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (7.7 g, 22.4) and N,N,N’,N’-tetramethylguanidine (3.39 mL, 26.9 mmol) in dimethyl sulfoxide (61 mL) is treated with 5-fluoro-2-chloropyrimidine (2.25 mL, 23.54 mmol) and the resulting solution is heated at 50 C. for 4 hours. The solution is cooled to room temperature and added to water (500 mL). The crude product is purified over silica gel using a 5 to 50% gradient of ethyl acetate/hexanes to give the title compound (7 g, 71%). ES/MS (m/e): 440 (M+H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 62802-42-0, 2-Chloro-5-fluoropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eli Lilly and Company; BECK, James Peter; GREEN, Steven James; LOPEZ, Jose Eduardo; MATHES, Brian Michael; MERGOTT, Dustin James; PORTER, Warren Jaye; RANKOVIC, Zoran; SHI, Yuan; WATSON, Brian Morgan; WINNEROSKI, JR, Leonard Larry; US2013/261111; (2013); A1;,
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Synthetic Route of 4595-61-3, 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. 4595-61-3, name is Pyrimidine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

5-pyrimidinecarboxylic acid 1.000 mmol was weighed at 2 ° CAnd 2-(7-oxobenzotriazole)-N,N,N’,N’-tetramethyluron hexafluorophosphate(HATU) 1.000 mmol was placed in a round bottom flask,Dissolved with 8mLDCM,After stirring for 10 min, N,N-diisopropylethylamine (DIPEA) was added 1.700 mmol.Stirring was continued for 10 min, and a solution of 5-methyl-7-(2-fluoro-4-aminophenoxy)-pyrazolo[1,5-a]pyrimidine 0.800 mmol in DCM was slowly added dropwise. After 10 min, the system was placed. Reaction at 35 ° C for 24 h,TLC detection;After the reaction is completed, the organic phase is washed three times with a saturated sodium chloride solution, and the reaction by-products are washed away.The organic phase was dried over anhydrous sodium sulfate and filtered to give a crude material.Pass through the column [V: V (ethyl acetate: petroleum ether) = 1:6],Get a white solid0.060g,That is, the product 7-[2-fluoro-4-(5-pyrimidinamide)phenoxy]-5-methylpyrazolo[1,5-a]pyrimidine(1H NMR and 13C NMR spectra are shown in Figure 7),The yield was about 42percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-61-3, its application will become more common.

Reference:
Patent; Guangzhou Medical University; Zhang Chao; Liang Xintong; Xie Guoquan; Luo Guolin; Wu Wenhao; Yu Lihong; (25 pag.)CN108727386; (2018); A;,
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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. 5305-45-3, name is 4,6-Dichloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below., Formula: C5HCl2N3

4,6-Dichloropyrimidine-5-carbonitrile (4.8 g, 27.59 mols) was suspended in 30 mL dioxane and the mixture was cooled at 0C in an ice bath. Ammonia solution (7N in methanol, 20 mL, 140 mmol) was added dropwise over 20 min. The mixture was stirred at 0C for 30 min. The solvent was evaporated and the crude was re-dissolved in tetrahydrofuran. A precipite was formed and filtered and washed with more tetrahydrofuran. The organics were evaporated under reduced pressure. The residue was purifed using a SP1Purification System (20%-80%, hexane-ethyl acetate) to give 2.38 g (56% yield) of the title compound as a white solid. Purity 100%.LRMS (m/z): 155 (M+1 )+

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, 5305-45-3, 4,6-Dichloropyrimidine-5-carbonitrile.

Reference:
Patent; ALMIRALL, S.A.; ERRA SOLA, Montserrat; CARRASCAL RIERA, Marta; TALTAVULL MOLL, Joan; CATURLA JAVALOYES, Juan Francisco; BERNAL ANCHUELA, Francisco Javier; PAGES SANTACANA, Lluis Miquel; MIR CEPEDA, Marta; CASALS COLL, Gaspar; HERNANDEZ OLASAGARRE, Maria Begona; WO2014/60432; (2014); A1;,
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.3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.Safety of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine

Synthesis of 7-(2-nitrobenzyloxy)methyl-7-deaza-2?-deoxyadenosine-5?-triphosphate6-Chloro-7-iodo-7-deazapurine (dA.23): Compound dA.23 was synthesized according to the procedure described by Ju et al. (2006, which is incorporated herein by reference). To a suspension of 6-chloro-7-deazapurine (1.00 g, 6.51 mmol) in anhydrous CH2Cl2 (55 mL) was added N-iodosuccinimide (1.70 g, 7.56 mmol). The reaction was protected from light while stirring at room temperature for two hours. The reaction was then concentrated down in vacuo. The material was re-crystallized from hot methanol to yield 6-chloro-7-iodo-7-deazapurine dA.23 (0.94 g, 52%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Lasergen, Inc.; Litosh, Vladislav A.; Hersh, Megan N.; Stupi, Brian P.; Wu, Weidong; Metzker, Michael L.; US9200319; (2015); B2;,
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Synthetic Route of 180869-36-7, 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 180869-36-7, name is 4-(Dimethoxymethyl)-2-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

b 2-Methylthiopyrimidine-4-carboxaldehyde The product of example 1(a) (9.96 g, 50 mmol), and 3N HCl (42 mL, 126 mmol) were combined and stirred at 48 C. for 16 h, cooled to 23 C., combined with EtOAc (200 mL) and made basic by the addition of solid Na2 CO3 (12.6 g, 150 mmol). The aqueous phase was extracted with EtOAc (4*150 mL, dried (Na2 SO4), concentrated and the residue was filtered through a pad of silica (ca 150 mL) with CH2 Cl2 to afford 7.49 g (97%) of the title compound 1 H NMR (CDCl3): delta9.96 (s,1), 8.77 (d, 1), 7.44 (d, 1), 2.62 (s,3).

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 180869-36-7, 4-(Dimethoxymethyl)-2-(methylthio)pyrimidine.

Reference:
Patent; SmithKline Beecham Corporation; US5756499; (1998); A;,
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. 14160-93-1, name is 4-Amino-6-chloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. name: 4-Amino-6-chloropyrimidine-5-carbaldehyde

6-Chloro-5-(2-methoxyvinyl)pyrimidin-4-ylamine (28) [0170] A suspension of (methoxymethyl)triphenylphosphonium chloride (276.0 g, 0.807 mol, 1.1 equiv) in THF (1.5 L) was cooled in an ice/salt bath to -2 C. and 1 M potassium tert-butoxide (KOtBu) in THF (807 mL, 0.807 mol, 1.1 equiv) was added over 1.5 h at -2 to -3 C. The deep red-orange mixture was stirred at -2 to -3 C. for 1 h. 4-Amino-6-chloropyrimidine-5-carbaldehyde (115.2 g, 0.7338 mol, 1.0 equiv) was then added portion wise to the reaction mixture as a solid form using THF (200 mL) to rinse the container and funnel. During the addition the reaction temperature increased from -3 to 13 C. and a brown color developed. When the reaction temperature dropped to 10 C., the cooling bath was removed and the reaction mixture was allowed to warm to ambient temperature and stirred at ambient temperature for 42 h. The reaction mixture was cooled to -2 C. before being quenched by the slow addition of saturated NH4Cl aqueous solution (750 mL). The mixture was concentrated under reduced pressure to remove most of the THF. The residue was partitioned between EtOAc (3 L) and H2O (1 L). The organic phase was filtered to remove insoluble material at the interface, then extracted with 2 N HCl (4×250 mL) followed by 3 N HCl (2×250 mL). The combined HCl extracts were back-extracted with EtOAc (500 mL) then filtered through Celite to remove insoluble material. The filtrate was cooled in an ice/brine bath, adjusted to pH 8 with a 6 N aqueous NaOH solution and extracted with EtOAc (3×1 L). The combined EtOAc extracts were washed with brine (1 L), dried over Na2SO4, stirred with charcoal (10 g) and silica gel (10 g) for 1 h. The mixture was filtered through Celite, washing the Celite pad with EtOAc (1 L). The filtrate was concentrated, co-evaporating residual EtOAc with n-heptane (500 mL). The resulting tan solid was pumped under high vacuum for 2 h to afford crude 6-chloro-5-(2-methoxyvinyl)pyrimidin-4-ylamine (72.3 g, 136.2 g theoretical, 53.1%). The crude desired product was used in the following reaction without further purification. A sample of crude product (2.3 g) was purified by silica gel column chromatography on, eluting with 0-35% EtOAc/n-heptane to give 1.7 g of pure 6-chloro-5-(2-methoxyvinyl)pyrimidin-4-ylamine as a white solid, which was found to be a 1 to 2 mixture of E/Z isomers. 1H NMR (300 MHz, DMSO-d6) for E-isomer: delta 8.02 (s, 1H), 7.08 (bs, 2H), 6.92 (d, 1H, J=13.1), 5.35 (d, 1H, J=13.0 Hz), 3.68 (s, 3H) ppm and for Z-isomer: delta 8.06 (s, 1H), 7.08 (bs, 2H), 6.37 (d, 1H, J=6.8 Hz), 5.02 (d, 1H, J=6.7 Hz), 3.69 (s, 3H) ppm; C7H8ClN3O (MW, 185.61), LCMS (EI) m/e 186/188 (M++H).

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, 14160-93-1, 4-Amino-6-chloropyrimidine-5-carbaldehyde.

Reference:
Patent; Incyte Corporation; Liu, Pingli; Wang, Dengjin; Wu, Yongzhong; Cao, Ganfeng; Xia, Michael; US2014/256941; (2014); A1;,
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