Pyrimidines

Application of 5466-43-3, 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 5466-43-3 as follows.

A mixture of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (0.47 g, 2.5 mmol), tert-butylamine (1.25 ml, 11.8 mmol) and isopropanol (5 ml) was heated at reflux for 8 to 18 hours. After evaporation of volatiles the mixture was purified by flash chromatography over silica gel to afford the title compound as a white solid (0.36 g, 64% yield).1HNMR (CDCl3, 300 MHz) delta 4.43 (bs, 1H), 2.87 (t, J=7.8 Hz, 2H), 2.58 (t, J=7.8 Hz, 2H), 2.15-2.07 (m, 2H), 1.47 (s, 9H).LC-MSD (ES+): (m/z) 226 [(M+H)+, 100].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5466-43-3, its application will become more common.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; US2010/144731; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 1753-50-0, name is 2-Chloropyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Chloropyrimidine-5-carbonitrile

To a stirred solution of compound BW (0.4 g, 2.86 mmol) in ethanol (10 mL), 2-chloropyrimidine-5-carbonitrile (AF, 0.77 g, 5.0 mmol) and DIPEA (2.6 mL, 14.3 mmol) were added and the reaction mixture was heated to 90C for 4h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 50% EtOAc/hexane to afford compound BX (0.5 g, 50%) as an off white solid. LC-MS: m/z 374.05 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 1753-50-0.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
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Application of 50593-92-5, 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. 50593-92-5, name is 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid, molecular formula is C6H5BrN2O2S, 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 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (110 g, 0.44 mol) in methanol (1.1 L) was cooled to 0C with stirreing. Thionyl chloride (50 mL, 0.66 mol) was added dropwise to the solution. The solution was slowly heated and the reaction was conducted under reflux with heating for four hours. The completion of the reaction was monitored by LC/MS and TLC and the solution was cooled to room temperature. The volatiles were distilled away under reduced pressure, and the residue was dissolved in ethyl acetate (1 L). The solution was washed with aqueous 10% sodium carbonate solution (200 mL) three times and with saturated brine (200 mL) twice. The resulting organic phase was dried over anhydrous magnesium sulfate. The solid was filtered out, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give the title compound (88 g, yield: 75%).

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 50593-92-5, 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid.

Reference:
Patent; Teijin Pharma Limited; MIZUNO, Tsuyoshi; SHIMADA, Tomohiro; UNOKI, Gen; MARUYAMA, Akinobu; SASAKI, Kosuke; YOKOSAKA, Takuya; TAKAHASHI, Hiroshi; HORIE, Kyohei; SAKAI, Yuri; (181 pag.)EP3546458; (2019); A1;,
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Related Products of 33097-11-9, 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 33097-11-9, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

4.17 6-Acetyl-7-methyl-2-(methylsulfanyl)pyrido[2,3-d]pyrimidine-4(3H)-one (13) To a stirred solution of aldehyde 1 (500 mg, 2.24 mmol) in 3.5 mL of DMF was added enamine 12 (250 mg, 2.52 mmol) followed by addition of a few drops of satd ethereal HCl. Mixture was stirred at ambient temperature for 5 h. Crystals formed were filtered, washed thoroughly with MeCN (10 mL) and dried at 110 C/5 Torr to give the titled compound (256 mg, 46%) as light pink powder, mp 265-267 C (MeCN; decomp.); numax(KBr) 3417 (br), 3008, 2731, 2625, 1726, 1716, 1690, 1627, 1524, 1426, 1371, 1345, 1263, 1227, 1163, 1108, 960, 794; deltaH (400 MHz, DMSO-d6, 60 C) 10.40 (1H, s, NH), 8.77 (1H, s, 5-H), 2.76 (3H, s, 7-CH3), 2.65 (3H, s, ?OCH3), 2.63 (3H, s, SCH3); deltaC (100.6 MHz, DMSO-d6, 60 C) 198.9 (COCH3), 165.1 (2-C), 164.0 (7-C), 161.3 (4-?), 157.3 (8a-C), 138.8 (5-C), 130.5 (6-C), 113.2 (4a-?), 29.8 (7-CH3), 24.6 (COCH3), 13.6 (SCH3); HRMS (ESI): MH+, found 250.0632. [C11H12N3O2S]+ requires 250.0645.

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 33097-11-9, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde.

Reference:
Article; Chizhova, Maria E.; Bakulina, Olga Yu.; Ivanov, Alexander Yu.; Lobanov, Pavel S.; Dar’in, Dmitrii V.; Tetrahedron; vol. 71; 36; (2015); p. 6196 – 6203;,
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Pyrimidine – Wikipedia

Application of 2972-52-3, 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. 2972-52-3, name is 2,4-Dichloro-5-pyrimidinecarbonyl chloride, molecular formula is C5HCl3N2O, 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.

To a solution of the 2,4-dichloropyrimidine-5-carbonyl chloride (24 mmol) in THF (24 ml) is added H2O (0.64 ml) at room temperature. The reaction mixture is stirred at room temperature for 0.83 h and then diluted with HaO. The mixture is extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacua to give the crude titled compound; 1H NMR (CDCI3) 5 6.80 (brs, 1H), 9.18 (s, 1H).

According to the analysis of related databases, 2972-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/18284; (2006); 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. 2380-63-4, name is 1H-Pyrazolo[3,4-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below., Product Details of 2380-63-4

A mixture of lH-Pyrazolo[3,4-d]pyrimidin-4-ylamine (11.75 g, 0.09 mol) (Step A) and N-iodosuccinimide (25.45 g, 0.11 mol) in dimethylformamide (300 ml) was stirred at 50 C for 24 hr. A second batch of N-iodosuccinimide (3.92 g, 0.02 mol) was added and the solution stirred for additional 24 hr. Upon standing at room temperature, a precipitate was formed which was separated by filtration and washed with dimethylformamide and ethanol to afford 10.05 g of the title compound. The filtrate was concentrated in vacuo to about one half of the original volume and 500 ml of water was added. The precipitated product was separated by filtration and washed with ethanol to afford a second batch of the product (10.53 g, combined yield 20.58 g, 90.6 %); LC/MS, API-ES, Pos, (M+H)+, 262.1.

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, 2380-63-4, 1H-Pyrazolo[3,4-d]pyrimidin-4-amine.

Reference:
Patent; FOLDRX PHARMACEUTICALS, INC.; WHITEHEAD INSTITUTE FOR BIOMEDICAL RESEARCH; WO2007/126841; (2007); A2;,
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Pyrimidine – Wikipedia

Electric Literature of 3435-25-4, Adding some certain compound to certain chemical reactions, such as: 3435-25-4, name is 4-Chloro-6-methylpyrimidine,molecular formula is C5H5ClN2, 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 3435-25-4.

General procedure: Synthesis of 2-methyl-5-((9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-yl)amino)isoindolin-1-one (4) Procedure A: A mixture of 9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-amine (3, 0.10 g, 0.37 mmol), 5-bromo-2-methylisoindolin-1-one (2, 0.10 g, 0.45 mmol), sodium tert-butoxide (54 mg, 0.56 mmol) and XPhos (5 mg, 0.01 mmol) in toluene (10 mL) was degassed with argon for 30 min. Tris(dibenzylideneacetone)dipalladium(0) (20 mg, 0.022 mmol) was added under argon atmosphere and the reaction mixture was heated at 100 C. for 12 h. After completion of the reaction, the reaction mixture was filtered through celite pad and the filtrate was concentrated. The crude residue was purified by silica gel column chromatography using 0-10% ethyl acetate in hexanes as eluent to afford 2-methyl-5-((9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-yl)amino)isoindolin-1-one (4). Yield: 0.11 g, 71%; MS (ESI) m/z 411 [M+1]+.

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. 3435-25-4, 4-Chloro-6-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 54326-16-8 , The common heterocyclic compound, 54326-16-8, name is 5-Chloropyrimidin-2(1H)-one, molecular formula is C4H3ClN2O, 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.

EXAMPLE 21 5-Chloro-1-(2-methoxyphenacyl)pyrimidin-2-one A solution of 5-chloropyrimidin-2-one (541 mg) and 2-bromo-2′-methoxyacetophenone (954 mg) in triethylamine (1 ml) and ethanol (25 ml) was stirred at ambient temperature for 31/2 hours. After evaporation of solvents, the residue was dissolved in ethyl acetate (150 ml) and this solution was washed with water (50 ml) and brine (25 ml), dried (MgSO4) and evaporated to give a foam. This was purified by preparative thin-layer chromatography on silica, developed in chloroform, then chloroform-ethanol (25:1) before crystallisation from ethyl acetate to give the title pyrimidinone (347 mg,); m.p. 123-125; lambdamax 248.5 nm epsilon 12200), 317.5 nm (epsilon 6700), lambdainf 229.5 nm (epsilon 12440), 349 nm (epsilon 2640).

The synthetic route of 54326-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Group Limited; US4636509; (1987); A;,
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Pyrimidine – Wikipedia

Electric Literature of 17573-78-3, 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.17573-78-3, name is 4,5,6-Trifluoropyrimidine, molecular formula is C4HF3N2, molecular weight is 134.06, as common compound, the synthetic route is as follows.

STR108 A solution of 42.4 g (0.45 mol) of phenol and 50.4 g (0.45 mol) of potassium tert-butoxide in 400 ml of tetrahydrofuran is added dropwise at 0 C. to a solution of 80 g (0.6 mol) of 4,5,6-trifluoropyrimidine in 1 l of tetrahydrofuran. When the addition was complete, the reaction mixture was stirred for 30 minutes at 0 C. and then poured into water and extracted using ethyl acetate. The organic phase is dried over sodium sulphate and concentrated in vacuo, and the residue is stirred with low-boiling petroleum ether. 63.8 g (68.1% of theory) of 4-phenoxy-5,6-difluoropyrimidine of melting point 65-66 C. are obtained.

Statistics shows that 17573-78-3 is playing an increasingly important role. we look forward to future research findings about 4,5,6-Trifluoropyrimidine.

Reference:
Patent; Bayer Aktiengesellschaft; US6103717; (2000); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 6972-27-6 , The common heterocyclic compound, 6972-27-6, name is 6-Chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, molecular formula is C6H7ClN2O2, 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.

Compound 6 (15 g, 74.5 mmol) was added portionwise to a cooled solution of cone. H2S04 (40 mL) . The reaction temperature was maintained below 10 C. Fuming nitric acid (15 mL) was added dropwise to the above reaction mixture and it was stirred for 2 h at the same temperature. The reaction nixture was poured onto the ice cold water (500 mL) and extracted with chloroform (2×260 mL). The combined organic extracts were washed with water (260 mL), dried over anhydrous Na2S04 and concentrated in vacuo to give the title compound (12.0 g) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta (ppm): 3.07 and 3.26 (both s, both 3H)

The synthetic route of 6972-27-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LATVIAN INSTITUTE OF ORGANIC SYNTHESIS; ARSENJANS, Pavels; VASILJEVA, Jelena; DOMRACHEVA, llona; SHESTAKOVA, Irina; GULBE, Anita; KANEPE-LAPSA, Iveta; KAUSS, Valerjans; KALVINS, Ivars; (33 pag.)WO2016/159747; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia