Category: 4595-59-9

Application of 4595-59-9, 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. 4595-59-9, name is 5-Bromopyrimidine, molecular formula is C4H3BrN2, 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 modified procedure of Rho and Abuh (Syn. Commun. 1994, 24, 253-256) was followed for the preparation of the titled aldehyde. Under nitrogen, to a solution of 5-bromopyrimidine (1 g, 6.3 mmol) in 60 mL anhydrous THF, was added BuLi (2.5 M, 2.6 mL, 6.5 mmol) at -78 C. The resulting yellow solution was stirred for 20 min, after which ethyl formate (0.55 mL, 6.7 mmol) was added dropwise over 5 min. After 20 min, the reaction was quenched with 1.5 M THF/HCl solution (4.5 mL, 6.7 mmol). The cold bathwas removed, and the reaction mixture was stirred for 1 h. THF was removed in vacco, 10 mL of water was then added. The mixture was extracted with CHCl3 (2*10 mL), and the combined organics were dried (MgSO4) and concentrated. The crude product was purified via flash column chromatography (5% MeOH/CHCl3) to give 0.35 g (51%) of the titled pyrimidine-5-carboxaldehydepyrimidine-5-carboxaldehyde.

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 4595-59-9, 5-Bromopyrimidine.

Reference:
Patent; Kosogof, Christi; Liu, Bo; Liu, Gang; Liu, Mei; Nelson, Lissa T. J.; Serby, Michael D.; Sham, Hing L.; Szczepankiewicz, Bruce G.; Xin, Zhili; Zhao, Hongyu; US2005/171131; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4595-59-9, 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. 4595-59-9, name is 5-Bromopyrimidine. A new synthetic method of this compound is introduced below.

To a solution of 5-bromopyrimidine (3 g, 18.87 mmol) in Et20 (120 mL) and THF (20ml) was added cyclopropylmagnesium bromide (39.6 mL, 19.81 mmol) at 0C. The resulting white suspension was stirred at rt for lh and quenched with water (0.340 mL, 18.87 mmol) followed by addition of DDQ (4.28 g, 18.87 mmol) in THF (10ml). The resulting black mixture was stirred at room temperature overnight. The reaction mixture was extracted with EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layer was washed with NaOH (IN) and brine. The crude product was purified by Biotage (0-15% EtOAc/hexanes, 1.2L) to afford the title compound (700 mg, 20%) as a yellow solid. XH NMR (500 MHz, CC13D) delta ppm 8.87 (1 H, s), 8.66 (1 H, s), 2.40-2.56 (1 H, m), 1.13-1.32 (4 H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4595-59-9, 5-Bromopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; FRENNESSON, David B.; SAULNIER, Mark G.; AUSTIN, Joel F.; HUANG, Audris; BALOG, James Aaron; VYAS, Dolatrai M.; WO2012/9510; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature 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.

General procedure: In the reaction tube with a magnetic bar was added the solution of aryl bromides (0.5 mmol) and phenylboronic acid (91 mg, 0.75 mmol), NaOH (24 mg, 0.6 mmol), complex 1 (0.0001-0.02 mol%, dissolved in DMA) and ethanol (3 mL). After stirred for the required time in the preset conditions, the reaction mixture was cooled to room temperature, and then quenched by 1 mL brine and 3 mL water, and extracted with ethyl acetate (3×5 mL). The combined organic layer was dried over anhydrous MgSO4 and the filtrate was concentrated to dryness under reduced pressure. The crude products were purified by column chromatography (petroleum ether, ethyl acetate) on silica gel.

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:
Article; Wu, Qinxu; Wu, Leilei; Zhang, Lei; Fu, Haiyan; Zheng, Xueli; Chen, Hua; Li, Ruixiang; Tetrahedron; vol. 70; 21; (2014); p. 3471 – 3477;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 4595-59-9, 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. 4595-59-9, name is 5-Bromopyrimidine, molecular formula is C4H3BrN2, 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.

6.34. Synthesis of (S)-2-Amino-3-(4-{2-amino-6-[2,2,2-trifluoro-1-(2-pyrimidin-5-yl-phenyl)-ethoxy]-pyrimidin-4-yl}-phenyl)-propionic acid A microwave vial (20 ml) was charged with 2-formylphenylboronic acid (290 mg, 2.0 mmol), 5-bromo-pyrimidine (316 mg, 2.0 mmol) and 8 ml of acetonitrile. To this mixture was added 4 ml of aqueous sodium carbonate (1M), followed by 100 mg of dichlorobis-(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated at 150 C. for 5 minutes with microwave irradiation. After cooling, the reaction mixture was extracted with ethylacetate. The organic layer was evaporated to provide a crude material, which was purified by ISCO to give 220 mg of 2-pyrimidin-5-yl-benzaldehyde.

According to the analysis of related databases, 4595-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jin, Haihong; Shi, Zhi-Cai; Tunoori, Ashok; Wang, Ying; Zhang, Chengmin; Devasagayaraj, Arokiasamy; US2008/153852; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4595-59-9, Adding some certain compound to certain chemical reactions, such as: 4595-59-9, name is 5-Bromopyrimidine,molecular formula is C4H3BrN2, 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 4595-59-9.

Dissolve 5-bromopyrimidine (50.0 g, 314.4 mmol) in triethylamine (400 mL), add copper (1) iodide (1.20 g, 6.2 mmol) and stir mixture under nitrogen. After 15 minutes, add trimethylsilyl acetylene (53.3 mL, 377.3 mmol), followed by dichlorobis (triphenylphosphine) palladium (II) (8.82 g, 12.5 mmol) and stir at room temperature. After 3 hours, filter the solution through Celiteo, rinsing with ether. Concentrate the filtrate under reduced pressure. Purification by flash chromatography on silica gel eluting first with hexanes (100%), then with hexanes: ethyl acetate (3: 1) gives the title compound : lH NMR (CDC13) 8 9. 10 (s, 1H), 8.77 (s, 2H), 0.27 (s, 9H).

According to the analysis of related databases, 4595-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2003/91226; (2003); 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

Reference of 4595-59-9, 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 4595-59-9, name is 5-Bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

In an autoclave, 1 equiv. of aryl halide or heteroaryl halide, 2 equiv. of 1-alkylimidazole, 0.1 equiv. of CuI, 0.2 equiv. of dried K4[Fe(CN)6] (potassium hexacyanoferrate(II)), tetradecane as an internal standard for the GC analysis and a suitable amount of toluene were combined under argon and heated to 160 C. (The K4[Fe(CN)6] was dried by heating powdered K4[Fe(CN)6]x3H2O in a vacuum of 1 mbar to 80 C. for at least 24 hours.) After 16 hours, the reaction mixture was cooled to room temperature. Conversion and yield were determinable by means of gas chromatography. An isolation of the product took place according to the customary workup (distillation, crystallization or chromatography).

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 4595-59-9, 5-Bromopyrimidine.

Reference:
Patent; Muller, Nikolaus; Magerlein, Wolfgang; Beller, Matthias; Schareina, Thomas; Zapf, Alexander; US2009/62541; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 4595-59-9 , The common heterocyclic compound, 4595-59-9, name is 5-Bromopyrimidine, molecular formula is C4H3BrN2, 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 3 N-((1R,2R)-2-Hydroxy-cyclohexyl)-6-(2-pyrimidin-5-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinamidea) 5-Trimethylsilanylethynyl-pyrimidine; Tetrakis(triphenylphosphine)palladium(O) (727 mg, 0.6 mmol) was added to a stirred, degassed suspension of 5-bromopyrimidine (5.0 g, 31.4 mmol) and copper(I)iodide (120 mg, 0.6 mmol) in toluene and diisopropylamine (1:1, 200 ml) under nitrogen. The reaction mixture was heated to 60 C., trimethylsilylacetylene (4.89 ml, 34.6 mmol) was added and the reaction mixture was stirred for 3 hours at 60 C.. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate (200 ml) and washed with saturated aqueous ammonium chloride solution (3¡Á100 ml). The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (5% ethyl acetate/heptane) to give 5-trimethylsilanylethynyl-pyrimidine as a pale brown solid, 4.71 g (85% yield). LC at 215 nm; Rt 2.07: 88%, m/z (ES+): 177 (M+H).

The synthetic route of 4595-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hebeisen, Paul; Roever, Stephan; US2008/70931; (2008); A1;,
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Pyrimidine – Wikipedia

Reference 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.

An oven dried 5 mL microwave vial with a 10 mm stir bar was charged with 5-bromopyrimidine (115 mg, 0.5 mmol), naphthalene-1-boronic acid (152 mg, 1.0 mmol) and tribasic potassium phosphate monohydrate (288 mg, 1.25 mmol). The vial was equipped with a septum and subjected to three evacuation/Argon backfill cycles. A toluene solution (0.1 mL) of Pd(OAc)2 (0.56 mg, 0.0025 mmol) and EvanPhos (1.8 mg, 0.0038 mmol) was added via syringe followed by toluene (0.9 mL). The reaction was stirred in an oil bath at 40 C. under argon. GC/MS monitoring showed complete consumption of the halide after 6 h. The vessel was cooled to rt and diluted with water (1 mL). The aqueous phase was extracted in flask with EtOAc (3*1 mL). The combined organic phases were flushed over a short plug of silica gel in a pasteur pipette and then washed with EtOAc. Volatiles were removed in vacuo. The mixture was chromatographed over silica gel eluting with 1:3 diethyl ether:hexanes (Rf=0.20, 3:7 diethyl ether:hexanes) which yielded an off-white powder (99 mg, 96%). 1H NMR (400 MHz, chloroform-d) delta 9.31 (s, 1H), 8.89 (s, 2H), 7.95 (dd, J=8.4, 3.7 Hz, 2H), 7.75 (d, J=8.2 Hz, 1H), 7.61-7.48 (m, 3H), 7.42 (d, J=7.0 Hz, 1H). 13C NMR (101 MHz, chloroform-d) delta 157.72, 157.40, 134.44, 133.87, 132.50, 131.26, 130.95, 129.53, 128.78, 127.84, 127.18, 126.54, 125.52, 124.65.

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; The Regents of the University of California; Lipshutz, Bruce H.; Handa, Sachin; Landstrom, Evan; (35 pag.)US2018/117574; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4595-59-9, 5-Bromopyrimidine, 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, 4595-59-9, blongs to pyrimidines compound. HPLC of Formula: C4H3BrN2

General procedure: A mixture of aryl bromides (0.5 mmol), potassium aryltrifluoroborates (0.6 mmol), K2CO3 (0.5 mmol), Pd(OAc)2 (1 mol %), EtOH/H2O (2 mL/2 mL) was stirred at 25 C in air for the indicated time. The reaction mixture was added to brine (15 mL) and extracted with ethyl acetate (3¡Á15 mL). The solvent was concentrated under vacuum, and the product was isolated by short-column chromatography on silica gel (200-300 mesh).

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:
Article; Liu, Chun; Li, Xinmin; Gao, Zhanming; Wang, Xinnan; Jin, Zilin; Tetrahedron; vol. 71; 23; (2015); p. 3954 – 3959;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia