Day: May 19, 2021

Adding a certain compound to certain chemical reactions, such as: 24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, 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, Application In Synthesis of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

LDA (2 M in cyclohexane/ethylbenzene/THF; 32.04 mL, 64.09 mmol) was added dropwise to a stirred solution of intermediate 115 (19 g, 61.03 mmol) in THF (244 mL) at -78 C to -60 C under nitrogen atmosphere. The mixture was stirred at -60 C for 40 minutes. Then 7-chloro-5-methyl-[l,2,4]triazolo[l,5-a]pyrimidine (CAS: 24415-66-5; 10.29 g, 61.03 mmol) dissolved in the minimum amount of THF was added dropwise and the mixture was stirred at -60 C to -70 C for 1 h. The mixture was quenched with NH4CI (aq. sat. soltn.) and concentrated in vacuo. The residue was partitioned between EtOAc and water. The layers were separated and the aqueous layer was extracted with EtOAc (x 2). The combined organic layers were dried (MgS04), filtered and concentrated in vacuo yielding intermediate 116 (27 g, 99.7% yield) used as such in the subsequent reaction step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres Avelino; ALCAZAR-VACA, Manuel Jesus; (192 pag.)WO2018/154133; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4595-59-9, 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 4595-59-9 as follows.

EXAMPLE 22A 5-Pyrimidin-5-yl-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic Acid Tert-Butyl Ester A mixture of the product of Example 6C (2.045 g, 9.63 mmol), 5-bromopyrimidine (1.84 g, 11.6 mmol), tris(dibenzylideneacetone)dipalladium (0) Pd2(dba)3, Strem, 0.265 g, 0.29 mmol), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, Strem, 0.30 g, 0.48 mmol) and tert-BuONa (sodium tert-butoxide, 1.85 g, 19.3 mmol) in 75 mL PhCH3 was degassed three times with a N2 back-flush. The mixture was warmed to 85 C., stirred for 48 h then was cooled, filtered and concentrated under reduced pressure. Purification by column chromatography (SiO2, 50% hexanes-EtOAc) gave 2.68 g of the title compound (9.23 mmol, 95% yield). MS (DCI/NH3) m/z 291 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-59-9, its application will become more common.

Reference:
Patent; Basha, Anwer; Bunnelle, William H.; Dart, Michael J.; Gallagher, Megan E.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Ryther, Keith B.; Tietje, Karin R.; US2005/65178; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 4994-86-9 ,Some common heterocyclic compound, 4994-86-9, molecular formula is C5H5ClN2, 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.

In a microwave tube 4-chloro-2-methylpyrimidine (50 mg, 0.3 89 mmol), 6- bromo-3-fluoro-2-methylpyridine (73.9 mg, 0.389 mmol), 1,1,1,2,2,2- hexamethyldistannane (127 mg, 0.389 mmol) and Pd(Ph3P)4 (22.47 mg, 0.019 mmol)were taken in DMF (4 mL). The reaction mixture was purged with nitrogen and heated at 160 C under microwave for 1 h. The reaction mixture was concentrated, diluted with brine and ethyl acetate. The organic layer was separated, dried over Na2SO4, filtered, and concentrated which afforded brownish oil. The crude product was purified by silica gel chromatography (20-40% ethyl acetate-hexane) to afford 4-(5-fluoro-6-methylpyridin-2-yl)-2-methylpyrimidine (72 mg, 0.354 mmol, 91% yield). LCMS (ESI) m/e 204.5 [(M+H), calcd for C11H11FN3 204.11; LC/MS retention time (method B): tR = 0.75 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4994-86-9, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 3993-78-0, name is 2-Amino-4-chloropyrimidine, molecular formula is C4H4ClN3, 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. SDS of cas: 3993-78-0

THF (20 mL) was added to a mixture of 4-chloro-2-aminopyrimidine (500 mg, 3.87 mmol) and N-Boc piperazine (7.21 g, 38.7 mmol). The reaction was stirred at 70 C. overnight. After cooling, the solvent was removed in vacuo and the remaining residue purified by silica gel chromatography (1:1 petroleum ether:ethyl acetate) to give tert-butyl 4-(2-aminopyrimidin-4-yl)piperazine-1-carboxylate (650 mg, 2.33 mmol, 60% yield). MS (ESI) calcd for C13H21N5O2: 279.2.

With the rapid development of chemical substances, we look forward to future research findings about 3993-78-0.

Reference:
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 131860-97-4, 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. 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. A new synthetic method of this compound is introduced below.

Methyl (£)-2-{2-[6-chloropyiimidin-4-yloxy]phenyl}-3-methoxyacrylate (E) (3g of 95.4% strength) was charged to the reaction tube followed by the solvent (10 ml) then 2- cyanophenol (1.2g), base (1.5 mol equivalents) and the compound being tested as a catalyst (15 mol%). The reaction mixtures were held, with stirring, at 400C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for formation of product, throughout the hold period, by Gas Chromatography. Results are recorded as area % levels of methyl (£)-2-{2-[6- chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (II) and methyl (E)-2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE l The results are shown in Table 2 below:TABLE 2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,131860-97-4, its application will become more common.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43977; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 39906-04-2, 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 39906-04-2, name is 4,6-Dichloro-2-methylpyrimidin-5-amine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 5-amino-4,6-dichloro-2-methyl-pyrimidine (5.6mmol) in acetonitrile (20mL), Cs2CO3 (11.2mmol) and the suitable arylisothiocyanate (5.6mmol) were added. The suspension was stirred at 50C until disappearance (5-30h) of the starting materials (TLC monitoring: eluting system ciclohexane/ethyl acetate 7:3). Then, another 50mL of acetonitrile was added and the suspension was heated at 50C and filtered while hot. The filtrate, after the addition of 5g of silica gel (70-230 mesh), was stirred at room temperature for 20min and filtered. The solvent was removed in vacuum, and the residue was collected and recrystallized.

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 39906-04-2, 4,6-Dichloro-2-methylpyrimidin-5-amine.

Reference:
Article; Varano, Flavia; Catarzi, Daniela; Squarcialupi, Lucia; Betti, Marco; Vincenzi, Fabrizio; Ravani, Annalisa; Varani, Katia; Dal Ben, Diego; Thomas, Ajiroghene; Volpini, Rosaria; Colotta, Vittoria; European Journal of Medicinal Chemistry; vol. 96; (2015); p. 105 – 121;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, 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, Product Details of 16019-33-3, blongs to pyrimidines compound. Product Details of 16019-33-3

1 g of 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde was dissolved in 20 mL of THF, and the reactor was cooled to -78 C. 4.36 mL of a methylmagnesium bromide diethyl ether solution (3 mol/L) was slowly added dropwise dropwisely thereto. At the same temperature, the mixture was stirred for 1 hour, and a saturated aqueous ammonium chloride solution was slowly added thereto to terminate the reaction. The reaction mixture was stirred at room temperature for 10 minutes and placed in a separatory funnel, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried over sodium sulfate to remove the solvent. The residue was purified by basic silica gel chromatography (hexane/ethyl acetate=1/0->3/1), thereby obtaining 446 mg of the title compound. (1322) Physical Properties: m/z [M+H]+ 207.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; MIYAZAKI, Isao; SHIMAMURA, Tadashi; KATO, Masanori; FUJITA, Hidenori; IGUCHI, Satoru; (161 pag.)US2018/9818; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 62802-42-0, 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.62802-42-0, name is 2-Chloro-5-fluoropyrimidine, molecular formula is C4H2ClFN2, molecular weight is 132.5235, as common compound, the synthetic route is as follows.

2 -chloro-5-fluoropyrimidine (50 g, 378.0 mmol) was stirred in a solution of HBr in AcOH (33 wt %, 250 mL) at 40 C for 16 h. The reaction mixture was then cooled to room temperature and the precipitate was collected by filtrate. The filter cake was dissolved in EtOAc (500 mL) and basified to pH = 9 with saturated Na2C03. The resulting mixture was extracted with EtOAc (500 mL x 2). The combined organic layers were washed with brine (100 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. PE (20 mL) was added into the residue and the precipitate was collected by filtration, then dried in vacuo to give 2303-A (35.0 g, 53%) as a light brown solid. MS 177.2 [M+H]+.

Statistics shows that 62802-42-0 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-fluoropyrimidine.

Reference:
Patent; RODIN THERAPEUTICS, INC.; FULLER, Nathan, Oliver; LOWE, John, A., III; (0 pag.)WO2020/14605; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 130049-82-0, 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 130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one. This compound has unique chemical properties. The synthetic route is as follows.

Example-8 Preparation of 3-(2-chloroethyl)-9-oxo-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (formula-9) A solution of oxalylchloride (8.8 ml) in dichloromethane (20 ml) was cooled to -65 C. and a solution of dimethyl sulfoxide (6.5 ml) dissolved in dichloromethane (20 ml) was added to it slowly and stirred for 30 min. keeping the temperature at -65 C. a solution of 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (5 grams) (formula-7) dissolved in dichloromethane (30 ml) was added to it very slowly and stirred for 40 min. Triethyl amine was added to the reaction mixture and then quenched with water. The organic layer was separated, washed with aqueous sodium carbonate and water. The solvent from the organic layer was distilled off under reduced pressure to provide the title compound. Yield: 4.0 grams

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 130049-82-0, 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one.

Reference:
Patent; MSN Laboratories Limited; Reddy, Manne Satyanarayana; Eswaraiah, Sajja; Satyanarayana, Revu; US8481729; (2013); B2;,
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. 308348-93-8, name is Methyl 2-aminopyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below., SDS of cas: 308348-93-8

Methyl 2-aminopyrimidine-5-carboxylate (300 mg, 2.0 mmol) was diluted in methanol (5 mL) containing a few drops of water. Lithium hydroxide (122 mg, 5.1 mmol) was added, and the reaction mixture was stirred at 60 C overnight. The mixture was concentrated under reduced pressure, then diluted in water and adjusted to pH 4 with 1 M HCI. 2- Aminopyrimidine-5-carboxylic acid precipitated as a white solid, which was isolated by vacuum filtration (244 mg, 90%): 1 H NMR (DMSO-cfe) delta: 12.73 (1 H, br s), 8.63 (2H, s), 7.44 (2H, br s).

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, 308348-93-8, Methyl 2-aminopyrimidine-5-carboxylate.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCOTT, William; LIU, Ningshu; MOeWES, Manfred; WO2012/62748; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia