Simple exploration of 2-(Tributylstannyl)pyrimidine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153435-63-3, its application will become more common.

Application of 153435-63-3, 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. 153435-63-3, name is 2-(Tributylstannyl)pyrimidine. A new synthetic method of this compound is introduced below.

A solution of 2-bromo-3-thiophene carboxylic acid (3.35 g, 16.2 mmol) in methanol (50 mL) was cooled to 0 C and saturated with gaseous HC1. The solution was heated to 60 C overnight, then concentrated in vacuo. The residue was redissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, and concentrated, providing methyl 2-bromothiophene-3-carboxylate as yellow oil. LRMS m/z (M+H) 221.1 found, 221.0 required. A solution of methyl 2-bromothiophene-3-carboxylate (1.74 g, 7.87 mmol), 2-(tributylstannyl)pyrimidine (4.36 g, 11.81 mmol), cesium fluoride (4.78 g, 31.5 mmol), and copper(I) iodide (0.450 g, 2.36 mmol) in DMF (16 mL) in a pressure vessel was purged subsurface with nitrogen and treated with palladium tetrakis (0.455 g, 0.394 mmol). The mixture was sealed and heated at 120 C overnight. The reaction was partitioned between ethyl acetate and water and filtered through celite. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel gradient chromatography (0-30% ethyl acetate in hexanes), providing methyl 2- (pyrimidin-2-yl)thiophene-3-carboxylate as a yellow solid. LRMS m/z (M+H) 221.2 found, 221.1 required. A solution of methyl 2-(pyrimidin-2-yl)thiophene-3-carboxylate (0.695 g, 3.16 mmol) and potassium trimethylsilanolate (0.506 g, 3.94 mmol) in THF (16 mL) was stirred at RT overnight, then diluted with ether and filtered through a glass frit. The solids were washed with ether, and the filtrate was concentrated, providing the title compound as a beige solid. LRMS m/z (M+H) 207.3 found, 207.1 required.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153435-63-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2015/95442; (2015); A1;,
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Introduction of a new synthetic route about 153435-63-3

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 153435-63-3, 2-(Tributylstannyl)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, SDS of cas: 153435-63-3, blongs to pyrimidines compound. SDS of cas: 153435-63-3

(S)-(5-(((5-chloropyridin-2-yl)amino)methyl)-6-azaspiro[2.5]octan-6-yl)(5-fluoro-2-(pyrimidin-2-yl)phenyl)methanone Intermediates 4 (1 eq) was dissolved dry DMF (20 ml/mmol), then CsF (2 eq), CuI (0.2 eq), [Ph3P]4Pd (0.1 eq) and 2-(tributylstannyl)pyrimidine (1.5 eq; prepared according to Eur. J. Org. Chem. 2003, 1711-1721) was added. The mixture was warmed at 130 C. for 10 minutes (microwave), then poured in aqueous saturated solution of NH4Cl and extracted with AcOEt. The organic layers were combined, dried (Na2SO4) and concentrated under vacuum; crude product was purified by silica gel column chromatography (DCM to DCM/MeOH 9/1) to obtain the title compound with yield of 15%. 1HNMR (CDCl3) delta ppm 8.80-8.93 (m, 1H), 8.64 (d, 1H), 8.24-8.50 (m, 1H), 7.83-8.08 (m, 1H), 6.89-7.40 (m, 4H), 6.17-6.56 (m, 1H), 5.11-5.25 (m, 1H), 4.3-4.9 (m, 1H), 3.6-4.0 (m, 2H), 3.01-3.47 (m, 2H), 1.92-2.38 (m, 1H), 1.45-1.8 (m, 1H), 0.65-1.12 (m, 1H), 0.17-0.59 (m, 4H). ESI+m/z 474 [M+Na]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ROTTAPHARM S.P.A.; Stasi, Luigi Piero; Rovati, Lucio; US2013/310400; (2013); A1;,
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Pyrimidine – Wikipedia

Some scientific research about 2-(Tributylstannyl)pyrimidine

According to the analysis of related databases, 153435-63-3, the application of this compound in the production field has become more and more popular.

Synthetic Route of 153435-63-3, Adding some certain compound to certain chemical reactions, such as: 153435-63-3, name is 2-(Tributylstannyl)pyrimidine,molecular formula is C16H30N2Sn, 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 153435-63-3.

A solution of the product from step 1 (1.74 g, 7.87 mmol), 2-(tributylstannyl)pyrimidine (4.36 g, 11.81 mmol), CsF (4.78 g, 31.5 mmol), and copper(I) iodide (0.450 g, 2.36 mmol) in DMF (16 mL) in a pressure vessel was sparged with nitrogen and treated with Pd(PPh3)4 (0.455 g, 0.394 mmol). The mixture was sealed and heated at 120 C overnight. The cooled reaction mixture was partitioned between EtOAc and water and filtered through celite. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-30% EtOAc in hexanes), to provide the title compound as a yellow solid. LRMS m/z (M+H) 221.2 found, 221.1 required.

According to the analysis of related databases, 153435-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; BESHORE, Douglas, C.; KUDUK, Scott, D.; LUO, Yunfu; MENG, Na; YU, Tingting; WO2015/20930; (2015); A1;,
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New learning discoveries about 153435-63-3

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Application of 153435-63-3, 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. 153435-63-3, name is 2-(Tributylstannyl)pyrimidine. A new synthetic method of this compound is introduced below.

Description 28: methyl 6-methyl-3-(2-pyrimidinyl)-2-pyridinecarboxylate (D28); To a suspension of methyl 3-iodo-6-methyl-2-pyridinecarboxylate D27 (300 mg), CsF (329 mg, 2.166 mmol) and Pd(Ph3P)4 (50.0 mg, 0.043 mmol) in DMF (10 ml) stirred under nitrogen at room temperature, was added 2-(tributylstannanyl)pyrimidine (480 mg, 1.299 mmol). The reaction mixture was stirred at 130 0C for 30 minutes in a microwave Personal Chemistry. The reaction mixture was partitioned between EtOAc and aqueous NaHCO3 saturated solution; the combined organic phases were dried to give the crude product, which was purified by silica gel chromatography (SNAP KP-NH 55 g; Cy/EtOAc from 100:0 to 70:30). Collected fractions were evaporated to obtain the title compound D28 (101 mg) as white solid. UPLC (Basic GEN_QC): rt = 0.56 minutes, peak observed: 230 (M+l). C12H11N3O2 requires 229. 1H NMR (400 MHz, DMSO-J6) delta ppm 8.92 (d, 2 H), 8.49 (d, 1 H), 7.44 – 7.63 (m, 2 H), 3.75 (s, 3 H), 2.57 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Introduction of a new synthetic route about 2-(Tributylstannyl)pyrimidine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153435-63-3, its application will become more common.

Reference of 153435-63-3, 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 153435-63-3 as follows.

To a suspension of methyl 3-iodo-6-methyl-2-pyridinecarboxylate D44 (300 mg), CsF (329 mg, 2.166 mmol) and Pd(Ph3P)4 (50.0 mg, 0.043 mmol) in DMF (10 ml) stirred under nitrogen at room temperature was added 2-(tributylstannanyl)pyrimidine (480 mg, 1.299 mmol). The reaction mixture was stirred at 130 C. for 30 minutes at microwave Personal Chemistry. The reaction mixture was partitioned between EtOAc and aqueous NaHCO3 saturated solution the combined organic phases were dried to give the crude product which was purified by silica gel chromatography (SNAP KP-NH 55 g; Cy/EtOAc 15 column volumes from 100/0 to 70/30). Collected fractions were evaporated to obtain the title compound D45 (101 mg) as white solid. UPLC (Basic GEN_C): rt=0.56 minutes, peak observed: 230 (M+1). C12H11N3O2 requires 229. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.92 (d, 2H), 8.49 (d, 1H), 7.44-7.63 (m, 2H), 3.75 (s, 3H), 2.57 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153435-63-3, its application will become more common.

Reference:
Patent; ALVARO, Giuseppe; Amantini, David; Castiglioni, Emiliano; Di Fabio, Romano; Pavone, Francesca; US2010/144760; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
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Share a compound : 2-(Tributylstannyl)pyrimidine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

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.153435-63-3, name is 2-(Tributylstannyl)pyrimidine, molecular formula is C16H30N2Sn, molecular weight is 369.1328, as common compound, the synthetic route is as follows.SDS of cas: 153435-63-3

6.01.15.01 4-H droxy-4-pyrimidin-2-yl-piperidine-l -carboxylic acid tert-butyl ester 9.9 mL 1.6 mol/L n-buthyllithium solution in hexane was added to 3.85 g 2-tributyl stannanyl- pyrimidine at -78 C. The reaction was stirred 30 min. at -78 C and 2.1 g 1- carboxylic acid tert- butyl ester-4-piperidone in 10 mL THF was added. The reaction mixture was warmed up and stirred at RT over night. Then, the reaction was cooled to 0 C, water and subsequently EtOAc were added and the layers were seperated. The organic layer was washed with water and with a saturated ammonia chloride solution. Then, the organic layer was dried and evaporated. The residue was purified by HPLC to yield 448 mg of the desiered product. Rt: 1.21 min (method B), (M+H)+: 280

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; WELLENZOHN, Bernd; WO2013/83741; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Introduction of a new synthetic route about 2-(Tributylstannyl)pyrimidine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153435-63-3, its application will become more common.

Adding a certain compound to certain chemical reactions, such as: 153435-63-3, 2-(Tributylstannyl)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, 153435-63-3, blongs to pyrimidines compound. Formula: C16H30N2Sn

General procedure: Intermediates (D19-22 and D25-31) (1 mmol) were dissolved in dry DMF (15 ml/mmol) under nitrogen atmosphere, then CsF (2 mmol), CuI (0.2 mmol), [Ph3P]4Pd (0.1 mmol) and pyrimidine-2-tributylstannane (1.5 mmol; prepared according to Eur. J. Org. Chem. 2003, 1711-1721) were added. The mixture was warmed at 130 C. for 10 minutes (microwave), then poured in aqueous saturated solution of NH4Cl and extracted with AcOEt (3×50 ml). The organic layers were combined, dried (Na2SO4) and concentrated under vacuum; the crude mixture was purified by silica gel column chromatography (Cyclohexane 100% to Cyclohexane/Acetone 8/2 or Cyclohexane 100% to cyclohexane/AcOEt 2/8) to give the title compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153435-63-3, its application will become more common.

Reference:
Patent; Stasi, Luigi Piero; Rovati, Lucio Claudio; US2015/65523; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Some scientific research about 2-(Tributylstannyl)pyrimidine

According to the analysis of related databases, 153435-63-3, the application of this compound in the production field has become more and more popular.

Electric Literature of 153435-63-3, Adding some certain compound to certain chemical reactions, such as: 153435-63-3, name is 2-(Tributylstannyl)pyrimidine,molecular formula is C16H30N2Sn, 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 153435-63-3.

Example 6 4-tert-butyl-7V-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-[2,2′]bipyrimi(iinyl- 4-yl] -benzenesu lfonam ide (Bosentan)To a solution of 13 (3 g, 5 mmol), dry cesium fluoride (1.7 g, 11 mmol) and bis(tri-t-butylphosphine)palladium (0) (255 mg, 0.5 mmol) in dry 1,4-dioxane (60 mL) was added 2-tributylstannyl pyrimidine (2.2 g, 6.0 mmol). The reaction mixture was stirred at 100-110 0C for 16 h under a stream of nitrogen, then cooled to room temperature and filtered through a pad of Celite. The filtrate was concentrated and the resulting residue was purified by column chromatography on silica gel. The title compound (2.23 g, 81 %) was obtained as a pale yellow solid. The crude bosentan was taken up in 6.7 mL of absolute ethanol at reflux. Water (6.7 mL) was added dropwise at reflux. The resulting suspension was allowed to slowly cool to 20-250C. The precipitate was filtered and air-dried at 250C to afford 2.0 g of bosentan monohydrate (70 % yield) as a white solid.1H-RMN (200 MHz, de-DMSO): 1.29 (s, 9H); 3.85 (m, 2H); 3.93 (s, 3H); 4.59 (m, 2H); 6.81-7.18 (m, 4H), 7.43 (d, J = 8.0 Hz, 3H); 8.45 (d, J = 8.0 Hz, 2H); 9.01 (s, 2H) ppm.DSC-TG: endothermic peak at 116.53 0C, with a loss of weight of 3.1 % (monohydrate).D10: 1.36 mum, D50: 20.32 mum, D90: 56.64 mum

According to the analysis of related databases, 153435-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INKE, S.A.; RODRIGUEZ ROPERO, Sergio; HUGUET CLOTET, Juan; WO2010/12637; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
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Share a compound : 2-(Tributylstannyl)pyrimidine

The synthetic route of 153435-63-3 has been constantly updated, and we look forward to future research findings.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 153435-63-3, name is 2-(Tributylstannyl)pyrimidine, the common compound, a new synthetic route is introduced below. Formula: C16H30N2Sn

38(a) ethyl N-{[6-hydroxy-7-(2-pyrimidinyl)-5-quinoxalinyl]carbonyl}glycinate. To a solution of ethyl N-[(7-bromo-6-hydroxy-5-quinoxalinyl)carbonyl]glycinate (0.120 g, 0.339 mmol) (prepared as in N2843-54-A1) in 1,4-dioxane (1.5 ml) was added 2-(tributylstannanyl)pyrimidine (0.138 g, 0.374 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.020 g, 0.017 mmol) followed by heating to 150 C. for 60 min. in a Biotage Initiator microwave synthesizer. Upon cooling, the reaction mixture was concentrated in vacuo and purified via flash column chromatography (0-100% ethyl acetate in hexane) to obtain ethyl N-{[6-hydroxy-7-(2-pyrimidinyl)-5-quinoxalinyl]carbonyl}glycinate (0.083 g, 0.235 mmol, 69.3% yield) as a pale orange solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 14.90 (s, 1H), 10.12 (t, J=5.8 Hz, 1H), 9.09 (s, 1H), 9.07 (s, 1H), 8.97 (d, J=1.8 Hz, 1H), 8.91 (d, J=2.0 Hz, 1H), 8.81 (s, 1H), 7.68 (t, J=4.9 Hz, 1H), 4.23 (d, J=5.8 Hz, 2H), 4.18 (q, J=7.2 Hz, 2H), 1.26 (t, J=7.2 Hz, 3H). MS (ES+) m/e 354 [M+H]+.

The synthetic route of 153435-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; US2010/305133; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Analyzing the synthesis route of 153435-63-3

According to the analysis of related databases, 153435-63-3, the application of this compound in the production field has become more and more popular.

Synthetic Route of 153435-63-3, 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 153435-63-3, name is 2-(Tributylstannyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 3-8 (Trans)-8-[(2,5′-bipyrimidin-2′-Vlamino)methyl]-3-(2-pyridinyl)-1-oxa-3-azaspiro[4.5]decan-2-one To a solution of (trans)-8-{[(5-bromo-2-pyrimidinyl)amino]methyl}-3-(2-pyridinyl)-1-oxa-3-azaspiro[4.5]decan-2-one (Intermediate 24, 30 mg, 0.072 mmol) in dimethylsulfoxide (3 ml) 2-(tributylstannanyl)pyrimidine (26.5 mg, 0.072 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.32 mg, 2.87 mumol) were added and the resulting mixture was irradiated in a microwave oven at 120 C. for 10 min. The crude solution was first eluted on a SCX cartridge (DCM/MeOH/NH3 (2M soln in MeOH) 100/0/0 to 80/10/10) and evaporated to dryness. Purification by silica gel chromatography (SP1 automated instrument, SNAP 10 g Si cartridge, elution in gradient with 0%-10% MeOHDCM) gave the title compound as a white solid (15 mg, 0.036 mmol, 50%).

According to the analysis of related databases, 153435-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Biagetti, Matteo; Contini, Stefania Anna; Genski, Thorsten; Guery, Sebastien; Leslie, Colin Philip; Mazzali, Angelica; Pizzi, Domenica Antonia; Sabbatini, Fabio Maria; Seri, Catia; US2009/203705; (2009); A1;,
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