Pyrimidines

Application of 108-53-2, 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 108-53-2, name is 2-Aminopyrimidin-4(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Step 1-Synthesis of 2-amino-5-nitro-3,4-dihydropyrimidin-4-one Concentrated sulfuric acid (2.4 mL) was added to 2-amino-3,4-dihydropyrimidin-4-one (1 g, 9.0 mmol). The mixture was stirred and cooled in ice bath before dropwise addition of concentrated nitric acid (0.56 mL). The mixture was stirred at RT for 30 min before being heated at 70 C. for 2 hr. The mixture was allowed to cool to RT and was slowly added to water (10 mL), cooled in an ice bath. The resultant precipitate was collected by suction filtration, washed with diethyl ether (5 mL) and then thoroughly dried under high vacuum to give the title compound: 1H NMR (250 MHz, DMSO) delta 7.18 (1H, br. s.), 8.61 (1H, br. s.), 8.81 (1H, s); LC-MS: m/z=+156.9 (M+H)+.

According to the analysis of related databases, 108-53-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; US2012/214762; (2012); A1;,
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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. 1801-06-5, name is 4-Chloro-5-fluoro-2-methoxypyrimidine. A new synthetic method of this compound is introduced below., Safety of 4-Chloro-5-fluoro-2-methoxypyrimidine

General conditions1: Chloropyrimidine 5 (0.45 mmol) and aminopyrazole 6 (0.30 mmol) were mixed in 1:1 acetic acid/water solution (1.4 mL) or in glacial acetic acid (1.4 mL) and stirred at 100 ¡ãC in an oil bath for 1 h (or 50 ¡ãC for 4 h or 25 ¡ãC for 18 h). The mixture was neutralized by the addition of ice-cold 5percent NaOH solution (10 mL) and extracted with methylene chloride (3 .x. 25 mL). Combined organic layers were dried and concentrated. The residue was further purified by normal phase flash chromatography (Biotage, for cPropylphenyl analogs R = C) or reversed phase preparative HPLC (analogs with free amines R = A or B), affording the desired aminopyrimidines (7-30).

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, 1801-06-5, 4-Chloro-5-fluoro-2-methoxypyrimidine.

Reference:
Article; Guo, Chuangxing; Dong, Liming; Marakovits, Joseph; Kephart, Susan; Tetrahedron Letters; vol. 52; 14; (2011); p. 1692 – 1696;,
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Reference of 13223-25-1, 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. 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, 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.

D-methyl lactate 0.46g (0.005 mol) and 2-Chloro-4,6-dimethoxy-pyrimidine 0.88g (0.005 mol) were dissolved in DMF 20 ml, K2CO3 0.52g (0.75 eq) was added thereto, and sodium methane sulfate 0.1g was added thereto, followed by stirring at 120C for 5 hours. The reacted solution was cooled to room temperature, and distilled under reduced pressure to obtain residue. The residue was extracted with cold water and ethylacetate three times, and washed with brine twice, the organic layer was dried with MgSO4, and the solvent was removed under reduced-pressure. Through purification with silica gel column chromatography, a target material 0.56g (46%) was obtained.: 1H NMR (300MHz, CDCl3) delta: 1.63(d, 3H), 3.73(s, 3H), 3.89(s, 6H), 5.22(q, 1H), 5.72(s, 1H).

According to the analysis of related databases, 13223-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SNU R&DB Foundation; Korea Research Institute Of Chemical Technology; EP2497768; (2012); A2;,
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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.287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate, molecular formula is C6H5ClN2O2, molecular weight is 172.57, as common compound, the synthetic route is as follows.name: Methyl 2-chloropyrimidine-5-carboxylate

Saturated aqueous sodium hydrogen carbonate solution (25.00 ml) was added to methyl 2-chloropyrimidine-5-carboxylate (0.863 g, 5 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (1.855 g, 6.00 mmol), palladium(II) acetate (0.056 g, 0.25 mmol) and triphenylphosphine (0.262 g, 1.00 mmol) in 1,2-dimethoxyethane (25.00 ml) at 25 C. under nitrogen. The resulting mixture was stirred at 80 C. for 4 h. The cooled reaction mixture was taken up in water (50 mL), washed with EtOAc (50 mL) and then the aqueous layer was acidified to pH1 with 2N HCl. The aqueous layer was extracted with EtOAc (3¡Á25 mL) and the combined organics washed with brine, dried over MgSO4 and concentrated under reduced pressure to afford 2-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine-5-carboxylic acid (1.280 g, 84%) as a yellow solid. This was used directly with no further purification. 1H NMR (399.9 MHz, DMSO-d6) delta 1.44 (9H, s), 2.65 (2H, q), 3.56 (2H, t), 4.15 (2H, m), 7.36 (1H, s), 9.18 (2H, s), 13.6 (1H, s). MS: m/z 304 (M-H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,287714-35-6, Methyl 2-chloropyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; US2008/153812; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1202759-91-8, N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

In a 50 mL 3-neck RBF equipped with a magnetic stirrer, calcium chloride guard tube and thermo pocket was charged N4-(3-aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxyl)phenyl)pyrimidine-2,4-diamine (0.40 g) in dry DCM (10 mL) and was cooled to -30 C. An acryloyl chloride solution in DCM (0.107 g in 5.0 mL DCM) was added slowly and the reaction mixture was stirred at -30 C. for approx. 40 minutes. The reaction was monitored on TLC using chloroform:methanol (9.6:0.4) as mobile phase. The reaction mixture was poured into water (100 mL) and basified using sodium bicarbonate. The reaction mixture was extracted with MDC (2*25 mL) and the combined organic layer was washed with 50 mL brine solution. The organic layer was dried over sodium sulfate and concentrated completely under reduce pressure at 40 C. Obtained solid was purified by triturating with diethyl ether (2*mL) and dried under vacuum to give 0.28 g N-(3-((5-fluoro-2-((4-(2-methoxyethoxyl)phenyl)amino)pyrimidin-4-yl)amino)phenyl)acrylamide.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1202759-91-8, N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Celgene Avilomics Research, Inc.; Tester, Richland; Chaturvedi, Prasoon; Zhu, Zhendong; Surapaneni, Sekhar S.; Beebe, Lisa; US2015/174128; (2015); A1;,
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Synthetic Route of 13544-44-0, Adding some certain compound to certain chemical reactions, such as: 13544-44-0, name is 2,4-Dichloro-5-iodopyrimidine,molecular formula is C4HCl2IN2, 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 13544-44-0.

To a solution of 2,4-dichloro-5-iodopyrimidine (27, 8.7 g, 31.6 mmol) and tert-butyl ((4-aminotetrahydro-2H-pyran-4-yl)methyl)carbamate (26, 5 g, 21.7 mmol) in DMAc (200 mL) was added NaHC03 (11.1 g, 132 mmol). After stirring at 80 C for 12 h, the reaction mixture was quenched with water (50 mL) and extracted with EtOAc (300 mL x 3). The combined organic phases were washed with water (200 mL x 2) and brine (100 mL), dried over Na2S04, filtered and concentrated in vacuo. The resulting residue was purified by column chromatography to provide tert-butyl ((4-((2-chloro-5-iodopyrimidin-4-yl)amino)tetrahydro- 2H-pyran-4-yl)methyl) carbamate (28, 5.02 g, 10.7 mmol).

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. 13544-44-0, 2,4-Dichloro-5-iodopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copelnad; (156 pag.)WO2018/5863; (2018); A1;,
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Electric Literature of 4595-59-9, 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.4595-59-9, name is 5-Bromopyrimidine, molecular formula is C4H3BrN2, molecular weight is 158.984, as common compound, the synthetic route is as follows.

General procedure: Method A: K3PO4 (531 mg, 2.5 mmol) was added to a solution of 5-bromopyrimidine (1) (159 mg, 1.0 mmol), phenylboronic (2a)[2-fluorobenzeneboronic acid (2b), 3-fluorobenzeneboronic (2c), 4-fluorobenzeneboronic (2d), 2,4-difluorobenzeneboronic (2e), 3,5-difluorobenzeneboronic (2f), 2-(trifluoromethyl)benzeneboronic (2g), 3-(trifluoromethyl)benzeneboronic (2h), 4-(trifluoromethyl)benzeneboronic (2i), 2,4-bis(trifluoro-methyl)benzeneboronic (2j), or 3,5-bis(trifluoro-methyl)benzeneboronic (2k) acids] (1.2 mmol) and trans-bis(dicyclohexylamine)palladium(II) acetate (29 mg, 0.05 mmol) in EtOH (10 mL). The resulting suspension was stirred at ambient temperature for 24 h. EtOH wasevaporated under a reduced pressure and the residue was suspendedin CH2Cl2 (20 mL) and filtered from inorganic salts. After that solvent was distilled off under a reduced pressure, and theresidue was purified by flash column chromatography on silicagel (hexane/ethyl acetate, 1:3) to afford the desired cross-coupling products (3a-k).

Statistics shows that 4595-59-9 is playing an increasingly important role. we look forward to future research findings about 5-Bromopyrimidine.

Reference:
Article; Verbitskiy, Egor V.; Baskakova, Svetlana A.; Kravchenko, Marionella A.; Skornyakov, Sergey N.; Rusinov, Gennady L.; Chupakhin, Oleg N.; Charushin, Valery N.; Bioorganic and Medicinal Chemistry; vol. 24; 16; (2016); p. 3771 – 3780;,
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Reference of 161489-05-0, 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 161489-05-0, name is 4-Iodo-6-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of(S)-4-(difluoromethyl)-N-(6-(3,4-dimethylpiperazin-1- yl)-2,4-difluoro-3 -(1,2,3 ,6-tetrahydropyridin-4-yl)phenyl)-6-oxo- 1 ,6-dihydropyridine- 3-carboxamide (31.5 mg, 0.064 mmol, preparation described in Example 34) and 2- bromo-5-methoxypyrimidine (16.89 mg, 0.089 mmol) in 2-propanol (2.5 mL) at RT was added N,N-diisopropylethylamine (0.022 ml, 0.128 mmol). After heating in a microwave reactor at 170 C for 2 h, the reaction mixture was purified on preparatory column eluting with water (containing 0.1% HCOOH)/acetonitrile (containing 0.1% HCOOH) gradient (85/55). The title compound was isolated as an yellow powder (20 mg, 50%). LCMS [M+1j 602.5.

According to the analysis of related databases, 161489-05-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROPELLON THERAPEUTICS INC.; AL-AWAR, Rima; ISAAC, Methvin; JOSEPH, Babu; LIU, Yong; MAMAI, Ahmed; PODA, Gennady; SUBRAMANIAN, Pandiaraju; UEHLING, David; WILSON, Brian; ZEPEDA-VELAZQUEZ, Carlos Armando; (311 pag.)WO2019/46944; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6153-44-2, Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate, 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, Recommanded Product: Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate, blongs to pyrimidines compound. Recommanded Product: Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

Methyl orotate (20.0 g, 118 mmol) was combined with iodine (12.8 g, 50 mmol) and periodic acid (4.8 g, 21 mmol) in methanol (250 mL) and heated at reflux for 20 h. After cooling to ambient temperature, the volatiles were removed by rotary evaporation. The solid residue was slurried in water, collected by filtration, washed well with water and dried under vacuum at 70¡ã C. to provide the title compound (34 g, 97percent yield) as a solid. It was used without further purification. MS: m/z=296.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6153-44-2, Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Dow AgroSciences LLC; US2009/88322; (2009); A1;,
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Related Products of 1004-39-3 ,Some common heterocyclic compound, 1004-39-3, molecular formula is C4H6N4S, 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.

PREPARATION 6 Synthesis of 4,6-diaminopyrimidine 167.78 g of 2-mercapto-4,6-diaminopyrimidine was dissolved in 1007 ml of 1.5N-aqueous sodium hydroxide solution, and the reaction solution was cooled down to 0 to 4 C. To this reaction solution was slowly added dropwise 267.55 g of 30% aqueous hydrogen peroxide solution. After the addition is completed, 170 ml of acetic acid was slowly added dropwise to the reaction solution to precipitate the solid product which was then filtered, washed successively with 200 ml of distilled water, 200 ml of methanol and 400 ml of diethylether and dried to obtain 185.56 g of the solid product as a white powder. The solid product thus obtained was slowly added to 1 L concentrated hydrochloric acid which was cooled to 0 C. to 4 C. The reaction solution was stirred for one hour at the same temperature, warmed to room temperature and then stirred for further 8 hours. The solid product produced during the reaction was filtered, washed with 1 L of acetone and 1 L of diethylether and then dried to obtain 109.13 g of the title compound in the form of hydrochloride salt. 109.13 g of the solid thus obtained was suspended in 400 ml of distilled water, and 200 ml of 15% aqueous sodium hydroxide solution was then added thereto. The mixture was stirred at room temperature for one hour and filtered. The filtered solid product was washed with 400 ml of ethanol and then dried to obtain 100.7 g of the title compound as a white powder. NMR (delta, DMSO-d6): 5.34(s, 1H), 6.01(s, 4H), 7.78(s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1004-39-3, its application will become more common.

Reference:
Patent; Lucky, Ltd.; US5541175; (1996); A;,
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