Pyrimidines

Synthetic Route of 7752-82-1 ,Some common heterocyclic compound, 7752-82-1, molecular formula is C4H4BrN3, 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 5-bromopyrimidin-2-amine (11 mmol, 2.0 g) in acetic acid (35 mL) was added sodium nitrite (69 mmol, 4.8 g) in water (25 mL) at RT over 1.5 h. After 5 h, the reaction mixture was partially evaporated, the precipitate was filtered and washed with water to give the title compound. MS (ESI) m/z = 175, 177 (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,7752-82-1, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SAKURADA, Isao; HIRABAYASHI, Tomokazu; MAEDA, Yoshitaka; NAGASUE, Hiroshi; MIZUNO, Takashi; XU, Jiayi; ZHANG, Ting; SMITH, Cameron; PARKER, Dann; WO2015/160634; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4983-28-2, Adding some certain compound to certain chemical reactions, such as: 4983-28-2, name is 2-Chloro-5-hydroxypyrimidine,molecular formula is C4H3ClN2O, 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 4983-28-2.

Intermediate 25: 2-Chloro-5-(3-methoxyphenoxy)pyrimidine A mixture of 2-chloro-5-hydroxypyrimidine (l .Og, 7.66mmol), 3-methoxyphenyl boronic acid (1.16g, 7.66mmol), copper (II) acetate (1.39g, 7.66mmol), triethylamine(5.34mL, 7.66mmol) and powdered 4A molecular sieves in dichloromethane (30mL) was stirred under air for 3 days. A calcium chloride guard tube was used to protect the reaction from moisture. The reaction mixture was diluted with dichloromethane, filtered and washed with water and brine. The organic phase was dried (MgS04), the solvent removed under reduced pressure and the crude product was purified by flash chromatography, using 0-15percent ethyl acetate:hexane as eluent, to provide 2-chloro-5- (3-methoxyphenoxy)-pyrimidine (0.448g, 25percent) as yellow oil.Mass: (ES+) 237 (M+H)+ NMR: deltaEta (CDC13) 3.82 (3H, s), 6.63 (2H, m), 6.81 (IH, br d), 7.33 (IH, t) and 8.39 (2H, s).

According to the analysis of related databases, 4983-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SENEXIS LIMITED; HORWELL, David Christopher; SCOPES, David Ian Carter; WO2011/144578; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1627-28-7, 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 1627-28-7, name is 6-Chloro-5-methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

A stirred solution of 6-chloro-5-methylpyrimidine-2,4(1 H,3H)-dione a5 (4.80 g, 0.30 mmol) and Nal (23.4 g, 150 mmol) in HI (60 mL) was stirred in sealed tube at room temperature for 66 h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was filtered and washed with cold water (50 mL) and dried under vacuum to afford 2.1 g of 6-iodo-5-methylpyrimidine-2,4(1 H,3H)-dione a6 was isolated as a brown solid, which was used in next step without any further purification. LCMS (ES+): 253 (M+H)+. 1H NMR (400 MHz, DMSO -cfe) 5 1 1.21 (s, 1 H), 1 .90 (s, 3H).

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 1627-28-7, 6-Chloro-5-methylpyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; UCB BIOPHARMA SPRL; MERCIER, Joel; VALADE, Anne; VERMEIREN, Celine; WOOD, Martyn; MAGUIRE, Ralph; (52 pag.)WO2019/105913; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, 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 131860-97-4, blongs to pyrimidines compound. Product Details of 131860-97-4

EXAMPLE 4 A solution of the potassium salt of 2-cyanophenol was prepared by mixing 2-cyanophenol (13.2 g) and potassium hydroxide (6.8 g) in water (7 g). This solution was added to (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (32.8 g) over 5 minutes while maintaining the temperature at 95-100 C. The resulting mixture was stirred at 120-20 C. for 2 hours. The reaction mixture was mixed with water and toluene and the organic layer separated. The toluene solution contained (E)-methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (61.5% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, and friends who are interested can also refer to it.

Reference:
Patent; ZENECA Limited; US6153750; (2000); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 57054-92-9, 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. 57054-92-9, name is 5-Bromo-2-chloro-4-methoxypyrimidine, molecular formula is C5H4BrClN2O, 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 stirred solution of 5-bromo-2-chloro-4-methoxypyrimidine (Intermediate 60, 60 mmol, 13.5 g) and 3-chloro-4-fluoroaniline (60.3 mmol, 9.23 g) in acetonitrile (140 mL), 4 M HCl in 1,4-dioxane (14 mL) was added dropwise. The resulting solution was refluxed at 100 C with constant stirring. The solvent was removed in vacuo and the residue was basified with 10% NaHCO3 solution, then extracted with ethyl acetate (2 x 250 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography (silicagel, 60-120 mesh) using 5% EtOAc in hexane to yield (5-bromo-4-methoxy-pyrimidin-2-yl)-(3-chloro-4-fluoro- phenyl)-amine as a white solid in 70 % yield (42 mmol, 14 g). MS(ES): 332 (M) for CnH8BrClFN3O.1H-NMR (400 MHz, DMSO-d6): delta 4.0 (s, 3H), 7.37 (t, J= 9.20 Hz, IH), 7.62 (ddd, J = 9.02, 4.12, 2.84 Hz, IH), 8.04 (dd, J= 6.80, 2.60 Hz, IH), 8.41 (s, IH), 9.94 (s, IH).

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 57054-92-9, 5-Bromo-2-chloro-4-methoxypyrimidine.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BORIACK-SJODIN, Ann; CARCANAGUE, Daniel, Robert; DUSSAULT, Daemian, David; HATOUM-MOKDAD, Holia; HULL, Kenneth, Gregory; IOANNIDIS, Georgine; MANCHESTER, John, Irvin; McGUIRE, Helen, Maureen; McKINNEY, David, Charles; STOKES, Suzanne; WO2010/38081; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 33097-13-1 ,Some common heterocyclic compound, 33097-13-1, molecular formula is C6H3Cl2N3S, 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.

[0440] Step 1 : To a suspension of 4,6-dichloro-2-(methylthio)pyrimidine-5-carbonitrile (330 mg, 1.5 mmol) in DMF (3 mL) was added 4-iodoaniline (361 mg, 1.65 mmol). After stirring at room temperature for 3 h, the mixture was diluted with water, the resulting precipitate was collected by filtration to give 4-chloro-6-(4-iodophenylamino)-2- (methylthio)pyrimidin-5-carbonitrile (541 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33097-13-1, its application will become more common.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; XU, Qing; HUANG, Wolin; JIA, Zhaozhong J.; SONG, Yonghong; WO2012/61415; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3764-01-0, 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.3764-01-0, name is 2,4,6-Trichloropyrimidine, molecular formula is C4HCl3N2, molecular weight is 183.42, as common compound, the synthetic route is as follows.

Under an atmosphere of nitrogen, a solution of morpholine (13.06 ml) in methylene chloride (100 ml) was added dropwise over 15 minutes to a stirred mixture of 2,4,6-trichloropyrimidine (27.52 g), triethylamine (22.1 ml) and methylene chloride (200 ml) that was cooled to a temperature between 50C and 15C. The resultant mixture was allowed to warm to ambient temperature and was stirred for 2 hours. The mixture was washed with anI0 aqueous brine solution. The organic solution was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using increasing proportions of ethyl acetate added to a 1:1 mixture of isohexane and methylene chloride as eluent. There was thus obtained 4,6-dichloro-2-morpholinopyrimidine (6.82 g); NMR Spectrum: (DMSOd6) 3.64-3.71 (m, 8H), 6.97 (s, IH); Mass Spectrum: M+H+ 234

Statistics shows that 3764-01-0 is playing an increasingly important role. we look forward to future research findings about 2,4,6-Trichloropyrimidine.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/32027; (2008); A1;,
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. 157335-97-2, name is 5-Bromo-4,6-dimethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 157335-97-2

1, 1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(ll)-dichloromethanecomplex (5 g, 6 mmol) was added to a degassed mixture of 2-(4-methoxy-2- methylphenyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (30 g, 120 mmol), 5-bromo-4,6- dimethylpyrimidine (22.5 g, 120 mmol), and potassium phosphate (76.3 g, 359 mmol) in 1,4-dioxane (300 mL) and water (150 mL). The reaction mixture was heated at reflux for4 hours, whereupon it was filtered and concentrated in vacuo. Purification via silica gel chromatography (Gradient: ethyl acetate in petroleum ether) provided the product as a brown solid. Yield: 25 g, 110 mmol, 92%. LCMS m/z229.3 [M+H]. 1H NMR (300 MHz, ODd3) oe 8.95 (5, 1H), 6.94 (d, J=8.2 Hz, 1H), 6.87-6.89 (m, 1H), 6.84 (dd, J=8.3, 2.5 Hz, 1H), 3.86 (5, 3H), 2.21 (5, 6H), 1.99 (5, 3H).

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, 157335-97-2, 5-Bromo-4,6-dimethylpyrimidine.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 355806-00-7, 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. 355806-00-7, name is (3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[(methanesulfonyl) methylamino]pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid tert-butyl ester. A new synthetic method of this compound is introduced below.

In a three-necked flask with a condenser, rosuvastatin tert-butyl ester 50.0g, 12.0g (+/-) – phenethylamine and 130ml toluene, stirring for reaction at 100 ~ 110 degrees for about 12 hours, the reaction was complete after HPLC detection of raw materials, slightly cooled, was added 80ml of water, rhoEta = 5 with concentrated hydrochloric acid, points to the water layer, the oil layer was concentrated to dryness to give a reddish brown oil. In the above oil Added 250ml methyl tert-butyl ether, warmed to a clear, refluxed 10min, naturally cooled to 25-30 C, a large amount of white solid Precipitation, stirring crystallization 2h, filtered and dried, weighed 49.5g, a yield of 91.0% by liquid detection, the corresponding isomer is 0.18%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,355806-00-7, its application will become more common.

Reference:
Patent; Zhejiang Jingxin Pharmaceutical Co., Ltd.; Shangyu Jing Xin Pharmaceutical Co., Ltd.; Zhu Jianrong; Zhong Hongban; Zhang Zhongliang; Wang Faping; Chen Jianyang; (8 pag.)CN104529908; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22536-63-6, 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. 22536-63-6, name is 2-Chloro-4-methoxypyrimidine. A new synthetic method of this compound is introduced below.

Under an argon atmosphere, sodium hydride (100 mg) was added to a solution of 4-iodoaniline (220 mg) and 2-chloro-4-methoxypyrimidine (145 mg) in anhydrous DMF (10 ml), and the resulting mixture was stirred at 125C for 21 hours. The reaction solution was cooled to room temperature and water was added thereto, followed by extracting the resulting mixture with ethyl acetate. Organic layer was washed twice with water and once with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate = 10/1) to obtain N-(4-iodophenyl)-4-methoxypyrimidin-2-amine (46 mg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22536-63-6, 2-Chloro-4-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Toray Industries, Inc.; EP2039687; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia