Category: 183438-24-6

Synthetic Route of 183438-24-6, 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.183438-24-6, name is 5-Bromo-2-iodopyrimidine, molecular formula is C4H2BrIN2, molecular weight is 284.88, as common compound, the synthetic route is as follows.

A mixture consisting of 5-bromo-2-iodopyrimidine (Bridge Organics, 10.0 g, 35.1 mmol), benzene boronic acid (Alfa Aesar, 4.25 g, 35.1 mmol), tetrakis(triphenylphosphine)palladium (Strem, 0.405 g, 0.351 mmol), toluene (150 mL), and a 2 M aqueous sodium carbonate solution (35 mL) was stirred at 115 C. (degrees Celsius) under a nitrogen atmosphere for 16 hours. After cooling to room temperature, the mixture was partitioned between chloroform (250 mL) and brine (200 mL). The phases were separated and the organic phase was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an orange oil (9.1 g). The crude product was purified by flash silica column chromatography. Elution through a 500-g Analogix flash silica cartridge with 100% hexanes afforded the title intermediate as a white solid (3.15 g, 38% yield). Rf 0.69 with 9:1 v/v hexanes-ethyl acetate; 1H-NMR (400 MHz; CDCl3) delta 8.83 (s, 2H), 8.44-8.38 (m, 2H), 7.52-7.46 (m, 3H); MS (APCI+) m/z 236.9 (M+1).

The chemical industry reduces the impact on the environment during synthesis 183438-24-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CAYMAN CHEMICAL COMPANY; US2010/75990; (2010); 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. 183438-24-6, name is 5-Bromo-2-iodopyrimidine. A new synthetic method of this compound is introduced below., Safety of 5-Bromo-2-iodopyrimidine

A mixture of potassium fluoride (1.77g) and cuprous iodide (5.79g) was stirred and heated together using a heat gun under vacuum (-1 mm) for 20min. After cooling, dimethyl formamide (20ml) and N-methyl pyrrolidinone (20ml) were added followed by (trifluoromethyl) trimethylsilane (4. 1ml) and 5-bromo-2-iodopyrimidine (6.5g). The mixture was stirred at rt for 5h and then the brown solution was poured into 6N ammonia solution. The product was extracted into ethyl acetate and the extracts were washed with sodium bicarbonate solution and brine and then dried (Na2SO4) and evaporated. Chromatography on silica gel (elution with 20-50% dichloromethane in pentane) gave the title compound (D13) as a white solid (2. 4g). 1 H NMR (CDC13) : 8.97 (2H, 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, 183438-24-6, 5-Bromo-2-iodopyrimidine.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/40144; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 183438-24-6 , The common heterocyclic compound, 183438-24-6, name is 5-Bromo-2-iodopyrimidine, molecular formula is C4H2BrIN2, 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.

A mixture of potassium fluoride (1.77g) and cuprous iodide (5.79g) was stirred and heated together using a heat gun under vacuum (-1 mm) for 20min. After cooling, dimethyl formamide (20ML) and N-METHYL PYRROLIDINONE (20ML) were added followed by (trifluoromethyl) trimethylsilane (4. 1ML) and 5-BROMO-2-IODOPYRIMIDINE (6.5g). The mixture was stirred at rt for 5h and then the brown solution was poured into 6N ammonia solution. The product was extracted into ethyl acetate and the extracts were washed with sodium bicarbonate solution and brine and then dried (NA2SO4) and evaporated. Chromatography on silica gel (elution with 20-50% DICHLOROMETHANE in pentane) gave the title compound (D30) as a white solid (2. 4G). 1 H NMR (CDCI3) : 8.97 (2H, s).

The synthetic route of 183438-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/101546; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 183438-24-6, 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 183438-24-6, name is 5-Bromo-2-iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 39; 5-Bromo-2-(2-fluorophenyl)pyrimidineA mixture of 5-bromo-2-iodopyrimidine (2.58 mmol, 0.500 g), 2-fluorophenylboronic acid (3.87 mmol, 0.542 g), 2M aqueous solution of K2CO3 (7.76 mmol, 3.9 ml), Pd(PPh3J4 in dioxane (12 ml) was heated at 11O0C overnight. The solvent was evaporated and the solid residue was extracted between water and ethyl acetate. The organic phase was evaporated and the crude residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate mixtures affording 0.466 g (yield 56%) of the expected product. ESI/MS (m/e, %): 253 [(M+1)+, 100], 255 [(M+1)+, 97].

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 183438-24-6, 5-Bromo-2-iodopyrimidine.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2009/21696; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 183438-24-6, 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 183438-24-6, name is 5-Bromo-2-iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a clean and dry reactor containing 20.04 g of isopropyl 2-bromo-3-cyclopentyl-1-methyl-1H-indole-6-carboxylate, 1.06 g of Pd(TFP)2Cl2 (3 mol %) and 0.76 g of tri(2-furyl)phosphine (6 mol %) was charged 8.35 g of triethylamine (1.5 equivalent), 39.38 g of CH3CN at 23±10 C. under nitrogen or argon and started agitation for 10 min 9.24 g of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane was charged into the reactor. The mixture was heated to reflux (ca. 81-83 C.) and stirred for 6 h until the reaction completed. The batch was cooled to 30±5 C. and quenched with a mixture of 0.99 g of water in 7.86 g of CH3CN. 17.24 g of 5-bromo-2-iodopyrimidine and 166.7 g of degassed aqueous potassium phosphate solution (pre-prepared from 46.70 g of K3PO4 and 120 g of H2O) was charged subsequently under argon or nitrogen. The content was heated to reflux (ca. 76-77 C.) for 2 h until the reaction completed. 4.5 g of 1-methylimidazole was charged into the reactor at 70 C. The batch was cooled to 20±3 C. over 0.5 h and hold at 20±3 C. for at least 1 h. The solid was collected by filtration. The wet cake was first rinsed with 62.8 g of 2-propanol, followed by 200 g of H2O. The solid was dried under vacuum at the temperature below 50 C. [0095] Into a dry and clean reactor was charged dried I, 10 wt % Norit SX Ultra and 5 V of THF. The content was heated at 60±5 C. for at least 1 h. After the content was cooled to 35±5 C., the carbon was filtered off and rinsed with 3 V of THF. The filtrate was charged into a clean reactor containing 1-methylimidazole (10 wt % relative to I). After removal of 5 V of THF by distillation, the content was then cooled to 31±2 C. After the agitation rate was adjusted to over 120 rpm, 2.5 V of water was charged over a period of at least 40 minutes while maintaining the content temperature at 31±2 C. After the content was agitated at 31±2 C. for additional 20 min, 9.5 V of water was charged into the reactor over a period of at least 30 minutes at 31±2 C. The batch was then cooled to about 25±3 C. and stirred for additional 30 minutes. The solid was collected and rinsed with 3 V of water. The wet product I was dried under vacuum at the temperature below 50 C. (19.5 g, 95 wt %, 76% yield).

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 183438-24-6, 5-Bromo-2-iodopyrimidine.

Reference:
Patent; Boehringer Ingelheim International GmbH; LI, Zhibin; YANG, Bing-Shiou; YIP, Kazuhiko; US2013/261134; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 183438-24-6, 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 183438-24-6, name is 5-Bromo-2-iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a clean and dry reactor containing 20.04 g of isopropyl 2-bromo-3-cyclopentyl-1-methyl-1H-indole-6-carboxylate, 1.06 g of Pd(TFP)2Cl2 (3 mol %) and 0.76 g of tri(2-furyl)phosphine (6 mol %) was charged 8.35 g of triethylamine (1.5 equivalent), 39.38 g of CH3CN at 23±10 C. under nitrogen or argon and started agitation for 10 min 9.24 g of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane was charged into the reactor. The mixture was heated to reflux (ca. 81-83 C.) and stirred for 6 h until the reaction completed. The batch was cooled to 30±5 C. and quenched with a mixture of 0.99 g of water in 7.86 g of CH3CN. 17.24 g of 5-bromo-2-iodopyrimidine and 166.7 g of degassed aqueous potassium phosphate solution (pre-prepared from 46.70 g of K3PO4 and 120 g of H2O) was charged subsequently under argon or nitrogen. The content was heated to reflux (ca. 76-77 C.) for 2 h until the reaction completed. 4.5 g of 1-methylimidazole was charged into the reactor at 70 C. The batch was cooled to 20±3 C. over 0.5 h and hold at 20±3 C. for at least 1 h. The solid was collected by filtration. The wet cake was first rinsed with 62.8 g of 2-propanol, followed by 200 g of H2O. The solid was dried under vacuum at the temperature below 50 C. [0095] Into a dry and clean reactor was charged dried I, 10 wt % Norit SX Ultra and 5 V of THF. The content was heated at 60±5 C. for at least 1 h. After the content was cooled to 35±5 C., the carbon was filtered off and rinsed with 3 V of THF. The filtrate was charged into a clean reactor containing 1-methylimidazole (10 wt % relative to I). After removal of 5 V of THF by distillation, the content was then cooled to 31±2 C. After the agitation rate was adjusted to over 120 rpm, 2.5 V of water was charged over a period of at least 40 minutes while maintaining the content temperature at 31±2 C. After the content was agitated at 31±2 C. for additional 20 min, 9.5 V of water was charged into the reactor over a period of at least 30 minutes at 31±2 C. The batch was then cooled to about 25±3 C. and stirred for additional 30 minutes. The solid was collected and rinsed with 3 V of water. The wet product I was dried under vacuum at the temperature below 50 C. (19.5 g, 95 wt %, 76% yield).

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 183438-24-6, 5-Bromo-2-iodopyrimidine.

Reference:
Patent; Boehringer Ingelheim International GmbH; LI, Zhibin; YANG, Bing-Shiou; YIP, Kazuhiko; US2013/261134; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 183438-24-6, 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. 183438-24-6, name is 5-Bromo-2-iodopyrimidine, molecular formula is C4H2BrIN2, 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 suspension of 5-bromo-2-iodopyrimidine (2.81 g, 9.86 mmol), vinyl boronic acid pinacol ester (1.98 mL, 11.7 mmol) and cesium carbonate (6.30 g, 19.5 mmol) in dioxane (39 mL) and water (14 mL) was degassed by sparging with Ar. [1,1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (364 mg, 486 mumol) was added and the reaction heated to 100 C for 4 h. The reaction mixture was concentrated in vacuo to remove the dioxane, then partitioned between EtOAc and water. The aqueous layer was extracted EtOAc (×2), then the combined organic layers dried (MgSO4), filtered and concentrated in vacuo. FCC (2-16% EtOAc in toluene) provided the title compound as an oil (0.850 g). 1H NMR (CDCl3, 300 MHz): delta 8.74 (s, 2H), 6.83 (dd, J = 17.4, 10.5 Hz, 1H), 6.62 (dd, J = 17.4, 1.8 Hz, 1H), 5.76 (dd, J = 10.5, 1.8 Hz, 1H).

According to the analysis of related databases, 183438-24-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRONNER, Sarah M.; CRAWFORD, James J.; CRIDLAND, Andrew; CYR, Patrick; FAUBER, Benjamin; GANCIA, Emanuela; GOBBI, Alberto; HURLEY, Christopher; KILLEN, Jonathan; LEE, Wendy; RENE, Olivier; VAN NIEL, Monique Bodil; WARD, Stuart; WINSHIP, Paul; ZBIEG, Jason; (439 pag.)WO2018/83105; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 183438-24-6, 5-Bromo-2-iodopyrimidine, 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, HPLC of Formula: C4H2BrIN2, blongs to pyrimidines compound. HPLC of Formula: C4H2BrIN2

Example 54: 5-bromo-2-(trifluoromethyl)pyrimidine:; A mixture of 1.77 g (30.35 mmoles, 1.33 eq.) of KF and 5.79 g (30.35 mmoles, 1.33 eq.) of CuI were stirred and heated together using a heat gun under vacuum (1 mm) for 20 min. After cooling, 20 ml_ of DMF and 20 ml of NMP were added followed by 4.1 ml_ (27.38 mmoles, 1.20 eq.) of CF3-TMS and 6.5 g (22.82 mmoles, 1.0 eq.) of 5-bromo-2- iodopyrimidine. The mixture was stirred at RT for 16h. The crude mixture was poured onto 200 ml_ of NH4OH 6N and the aqueous phase was extracted six times with 50 mL of AcOEt. The combined organic layers were washed three times with 50 mL of a saturated solution of Na2CO3, once with 50 mL of brine, dried over Na2SO4, filtered and evaporated to dryness. The crude compound was purified by flash chromatography on silica gel to give 940 mg of a white solid.Yield : 18 % M.P. : 33-39C EPO LC-MS : T1. = 4.32 min. (100 %) (no ionization)) [Column : Nucleosil C-18HD, 4×70 mm, 3mum, gradient CH3CN/H2O/TFA 0.05% : 20-100% CH3CN (6 min.), 100% CH3CN (1.5 min.), flow : 1 mL/min].1H-NMR (CDCI3, 300 MHz) delta : 8.93 (s, 2H). 19F-NMR (CDCI3, 282 MHz) delta : -70.8.

The synthetic route of 183438-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/136442; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 183438-24-6, 5-Bromo-2-iodopyrimidine, 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, Formula: C4H2BrIN2, blongs to pyrimidines compound. Formula: C4H2BrIN2

Step 1: 5-Bromo-2-phenyl-pyrimidine To a degassed solution of phenylboronic acid (8.93 g, 73.22 mmol, 1.0 equiv; commercially available), 5-bromo-2-iodo-pyrimidine (20.86 g, 73.22 mmol, 1.0 equiv; commercially available) and tetrakis(triphenylphosphine) palladium(0) (0.85 g, 0.73 mmol, 0.01 equiv) in toluene (180 mL) was added Na2CO3 (15.52 g, 146.45 mmol, 2.0 equiv), dissolved in water (60 mL), and the reaction mixture heated to reflux. After 18 h, tetrakis(triphenylphosphine) palladium(0) (0.42 g, 0.37 mmol, 0.005 equiv) was added and the reaction mixture heated for an additional time period of 24 h. The solvent was removed under reduced pressure and the crude reaction product extracted from a sat. solution of NaCl (200 mL) with ethyl acetate (3*150 mL). The combined organic phases were dried over Na2SO4, concentrated by evaporation under reduced pressure and the crude material purified by silica column chromatography eluding with heptane/ethyl acetate (9:1) to provide 8.60 g (50percent) of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,183438-24-6, 5-Bromo-2-iodopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Christ, Andreas D.; Martin, Rainer E.; Mohr, Peter; US2008/64697; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 183438-24-6, 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. 183438-24-6, name is 5-Bromo-2-iodopyrimidine, molecular formula is C4H2BrIN2, 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.

5-Bromo-2-iodopyrimidine (2 g, 7.02 mmol) was dissolved in dry toluene (30 mL) and cooled to -78 C under nitrogen. A 2.5M solution of n-BuLi in hexane (2.95 mL) was added drop wise and the reaction stirred for 15 minutes prior to the drop wise addition of tetrahydro-4H-pyran-4-one (0.77 g, 7.72 mmol). The reaction was stirred at -78 C for 30 min and then was allowed to warm to r.t.. The reaction mixture was diluted with water – -(50 mL) and extracted with EtOAc (2 x 50mL). The combined organic extracts were dried over magnesium sulfate and the solvent removed under reduced pressure to afford 1.9 lg of crude product as an orange oil. The crude orange oil was purified by flash column chromatography (Si02, 10-100% EtOAc in heptane) to afford 762 mg (42 %) of the title compound as a yellow oil.1H NMR (500 MHz, CDC13) delta ppm 8.79 (s, 2H), 4.24 (s, 1H), 3.99 – 3.89 (m, 4H), 2.37 (td, J 12.3, 11.6, 6.3 Hz, 2H), 1.54 (dd, J 13.6, 2.0 Hz, 2H).

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 183438-24-6, 5-Bromo-2-iodopyrimidine.

Reference:
Patent; UCB BIOPHARMA SPRL; ALEXANDER, Rikki, Peter; BRACE, Gareth, Neil; BROWN, Julien, Alistair; CALMIANO, Mark, Daniel; CHOVATIA, Praful, Tulshi; DELIGNY, Michael; GALLIMORE, Ellen, Olivia; HEER, Jag, Paul; JACKSON, Victoria, Elizabeth; KROEPLIEN, Boris; MAC COSS, Malcolm; QUINCEY, Joanna, Rachel; SABNIS, Yogesh, Anil; SWINNEN, Dominique, Louis, Leon; ZHU, Zhaoning; WO2015/86526; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia