Category: pyrimidines

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. 149765-15-1, name is N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide, molecular formula is C11H13ClN4O, 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. COA of Formula: C11H13ClN4O

4-Chloro-5-iodo-2-trimethylacetamido-pyrrolor2.3-(flpyrimidine (9b).4-Chloro-2-trimethylacetamido-pyrrolo[2,3-rf]pyrimidine (9a, 10.9 g, 43.24 mmol) was dissolved in anhydrous THF (120 mL) under nitrogen. After the addition of LambdaModosuccinimide (10.7 g, 47.56 mmol), the mixture was stirred at RT for 1 h. The solvent was then removed in vacuo. The residue dissolved in EtOAc (100 mL) and washed with 1 M sodium thiosulfate (3×100 mL). Column chromatography purification (2% MeOH in DCM, isocratic ) yielded 9b (12.9 g). 1H-NMR (DMSO-rfbeta): 1.2 (9H, s), 7.8 (IH, d, Ji = 4 Hz), 10.1 (IH, s), 12.7 (IH, s).

With the rapid development of chemical substances, we look forward to future research findings about 149765-15-1.

Reference:
Patent; BENNER, Steven, Albert; HUTTER, Daniel; LEAL, Nicole, Aurora; KARALKAR, Nilesh, Bhaskar; WO2010/110775; (2010); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3438-55-9, 5-Bromo-4-chloro-6-methylpyrimidine, 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 C5H4BrClN2, blongs to pyrimidines compound. Computed Properties of C5H4BrClN2

Sodium methoxide (25 wt% solution in methanol, 1.83 mL, 16.0 mmol) was added to a solution of 5-bromo-4-chloro-6-methylpyrimidine (1.85 g, 8.92 mmol) in methanol (50 mL) and the reaction was stirred at ambient temperature for 1 hour. The reaction was quenched by the addition of pH 7 buffer. The majority of the methanol was removed under reduced pressure. The aqueous portion was diluted with water and was extracted with diethyl ether three times. The combined organic extracts were washed with brine, dried over Na2S04, filtered and concentrated to afford 5- bromo-4-methoxy-6-methylpyrimidine (1.43 g, 79%). ¹H NMR (CDC13, 400 MHz): 8 8.48 (s, 1H); 4.00 (s, 3H); 2.54 (s, 3H). MS (ES) 204(M+1).

The synthetic route of 3438-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; WO2005/105814; (2005); A1;,
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Pyrimidine – Wikipedia

Application of 959236-97-6, 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.959236-97-6, name is 4-Bromo-2-(methylthio)pyrimidine, molecular formula is C5H5BrN2S, molecular weight is 205.08, as common compound, the synthetic route is as follows.

General procedure: In two neck 50 mL round bottom flask dry under nitrogen ethylN-imidazo[1,2-b]pyridazin-6-ylcarbamate (0.104 g, 0.66 mmol) was placed inanhydrous toluene (2.1 mL). After 10 min, 3-bromopyridin (0.083 mL, 0.66 mmol),Pd(OAc)2 (0.045 g, 10%), triphenylphosphine(0.035 g,20%), was added and then K2CO3 (0.184 g, 1.29mmol). The mixture was heated at 110C during 8 h. After cooling to roomtemperature, the solvent was evaporated. The crude residue was diluted in AcOEtand washed with NaCl solution. The organic layer was dried over Na2SO4,filtered, and evaporated under reduced pressure. The crude residue was purifiedby chromatography on silica gel using Cyclohexane-AcOEt (7:3). Evaporation ofthe eluent in vacuum gave the desired compound in 6.8% yield (0.013 g) as awhite powder.

Statistics shows that 959236-97-6 is playing an increasingly important role. we look forward to future research findings about 4-Bromo-2-(methylthio)pyrimidine.

Reference:
Article; Bendjeddou, Lyamin Z.; Loaec, Nadege; Villiers, Benoit; Prina, Eric; Spaeth, Gerald F.; Galons, Herve; Meijer, Laurent; Oumata, Nassima; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 696 – 709;,
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Pyrimidine – Wikipedia

Related Products of 31462-58-5, 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.31462-58-5, name is 5-Iodopyrimidine, molecular formula is C4H3IN2, molecular weight is 205.9845, as common compound, the synthetic route is as follows.

General procedure: To a round-bottom flask, aryl electrophile (1.0mmol), Pdnanocatalyst (1.5 mol%), Cs2CO3(1.5 mmol), PhB(OH)2(1.3 mmol), and EtOH (3.0 mL) were added, stirred andheated at 80C. The progress of the reaction was checked using TLC. After the completion of the reaction, the mixturewas cooled down and the catalyst was isolated usingan external magnet. The solvent was evaporated and furtherpurification was achieved using column chromatography onsilica gel to deliver the desired biphenyl derivatives in highyields.

The chemical industry reduces the impact on the environment during synthesis 31462-58-5, I believe this compound will play a more active role in future production and life.

Reference:
Article; Khalili, Dariush; Banazadeh, Ali Reza; Etemadi-Davan, Elham; Catalysis Letters; vol. 147; 10; (2017); p. 2674 – 2687;,
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Pyrimidine – Wikipedia

Application of 34253-03-7, 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 34253-03-7, name is Methyl pyrimidine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl pyrimidine-2-carboxylate (25 g, 181 mmol, 1 equiv) in MeOH (500 mL) was added NaBHt (8.2 g, 217 mmol, 1.2 equiv) at 0C. The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was quenched with H2O (20 mL), concentrated in vacuo and the residue was purified by flash column chromatography (eluted with PE/EtOAc = 1/1) to afford the title compound pyrimidin-2- ylmethanol as a yellow oil (16 g, 80% yield). LC-MS : m/z 111.0 (M+H)+

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 34253-03-7, Methyl pyrimidine-2-carboxylate.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
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Pyrimidine – Wikipedia

Reference of 199678-12-1, Adding some certain compound to certain chemical reactions, such as: 199678-12-1, name is 4-Pyrimidin-2-yl-benzoic acid,molecular formula is C11H8N2O2, 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 199678-12-1.

General procedure: This compound was prepared by means of a procedure similar to that used for 7g and 7a. Under an argon atmosphere, diethyl cyanophosphonate (DEPC) (0.09 mL, 0.61 mmol) and triethylamine (0.18 mL, 1.30 mmol) were added to a solution of compound 9 (246 mg, 0.47 mmol) and 4-(2-pyridyl)benzoic acid (94 mg, 0.47 mmol) in dehydrated N,N-dimethylformamide (10 mL) at 0 C. The reaction mixture was left to stand overnight, then poured into a saturated aqueous solution of sodium hydrocarbonate, and the whole was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluant; n-hexane/ethyl acetate = 1:2 v/v) to afford the intermediate compound.

According to the analysis of related databases, 199678-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ohashi, Masao; Oyama, Takuji; Putranto, Endy Widya; Waku, Tsuyoshi; Nobusada, Hiromi; Kataoka, Ken; Matsuno, Kenji; Yashiro, Masakazu; Morikawa, Kosuke; Huh, Nam-Ho; Miyachi, Hiroyuki; Bioorganic and Medicinal Chemistry; vol. 21; 8; (2013); p. 2319 – 2332;,
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Pyrimidine – Wikipedia

Electric Literature of 313339-35-4, 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 313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 3pyrimidin-5-yl1carbonyl}amino]phenyl>cvclohexyl acetate.A 50-mL 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was charged with a solution of 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid (700 mg, 2.93 mmol, 1.50 equiv) and N^V-dimethylformamide (1 drop) in dichloromethane (10 mL). The solution was treated with oxalyl chloride (750 mg, 5.91 mmol, 3.00 equiv) dropwise with stirring, stirred for 2 h at room temperature and then treated with a solution of Intermediate 2 (800 mg, 1.97 mmol, 1.00 equiv) in dichloromethane (10 mL) and DIEA (2 mL) dropwise with stirring at 0C. The resulting solution was stirred for an additional 1 h at room temperature, concentrated under vacuum and the residue was purified by chromatography on silica gel (1 :10 ethyl acetate/petroleum ether) to afford the title compound as a colorless oil. HPLC/MS: 626.31 (M+H); Rt 4.78 min (LC4).

According to the analysis of related databases, 313339-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GRAHAM, Thomas, H.; SHEN, Dong-Ming; NARGUND, Ravi, P.; DEVITA, Robert, J.; YU, Yang; LIU, Wensheng; WO2012/122075; (2012); A1;,
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Pyrimidine – Wikipedia

Application of 3438-61-7 ,Some common heterocyclic compound, 3438-61-7, molecular formula is C5H7N3, 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.

To a solution of 4-methylpyrimidin-5-amine (1) (3.0 g, 27.5 mmol) and pyridine (10.9 g, 0.137 mol) in DCM (30 mL) was added methanesulfonyl chloride (6.3 g, 55.0 mmol) at 0 C. and the resulting mixture was stirred at 20 C. for 3 hours. TLC showed the reaction was completed. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give N-(4-methylpyrimidin-5-yl)methanesulfonamide (2) (1.0 g, 19.4%) as yellow solid. 1H NMR (400 MHz, CHCl3-d) delta ppm 8.98 (s, 1H), 8.76 (s, 1H), 6.68 (br s, 1H), 3.13 (s, 3H), 2.61 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3438-61-7, its application will become more common.

Reference:
Patent; ESSA Pharma, Inc.; Zhou, Han-Jie; Virsik, Peter; (216 pag.)US2020/123117; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 882670-89-5, 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 882670-89-5, name is 6-Bromopyrido[2,3-d]pyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 6-(3 ,5 -dimethoxyphenyl)pyrido [2,3-d]pyrimidin-2-amine. A mixture of 6-bromopyrido[2,3-d]pyrimidin-2-amine (1.0 g, 4.46 mmol), 3,5- dimethoxyphenylboronic acid (1.2 g, 6.70 mmol), PdC12(dppf) (364 mg, 0.446 mmol) and potassium carbonate (1.8 g, 13.39 mmol) in 1,4-dioxane/water (4 mL/1 mL) was degassed withnitrogen for 5 mm and stirred at 110 C for 30 mm under microwave. The reaction mixture was cooled to RT, and concentrated to afford a crude product, which was purified by silica gel column chromatography (ethyl acetate:petroleum ether = 4: 1) to afford 6-(3,5- dimethoxyphenyl)pyrido[2,3-d]pyrimidin-2-amine as a yellow solid (400 mg, 31%). MS (ES+) C15H14N402 requires: 282, found: 283 [M+H].

According to the analysis of related databases, 882670-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUEPRINT MEDICINES; BIFULCO, Neil, Jr.; BROOIJMANS, Natasja; HODOUS, Brian, L.; KIM, Joseph, L.; MIDUTURU, Chandrasekhar, V.; WO2014/11900; (2014); A2;,
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Pyrimidine – Wikipedia

Application of 29939-37-5, 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. 29939-37-5, name is 4-Hydroxy-6-hydrazinylpyrimidine. A new synthetic method of this compound is introduced below.

A mixture comprising 5.0 g (39.6 mmol) 6-hydrazinopyrimidin-4-ol/6- hydrazinopyrimidin-4(1 H)-one (CAS-No: 29939-37-5), 5.12 g pentan-3-one and 80.8 mL ethanol was heated under reflux for 2 hours. After cooling to 3C, the precipitated solid was filtered off and washed with diethyl ether to give 5.82 g (72%) of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29939-37-5, 4-Hydroxy-6-hydrazinylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KLAR, Ulrich; WORTMANN, Lars; KETTSCHAU, Georg; PUeHLER, Florian; LIENAU, Philip; PETERSEN, Kirstin; HAeGEBARTH, Andrea; SUeLZLE, Detlev; GRAHAM, Keith; RICHTER, Anja; WO2014/48869; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia