Category: 22276-95-5

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. 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (E-2) (2.33 g, 10.0 mmol, 1.0 eq) in anhydrous THF (100 mL) at -78 C under argon, n-BuLi solution (2.5 M in THF, 8.8 mL, 22.0 mmol, 2.2 eq) is added dropwise (over 10 min). The resulting mixture is stirred at -78 C for lh and then DMF (2.0 g, 11.0 mmol, 1.1 eq) is added dropwise (over 10 min). The mixture is stirred at -78 C for an additional 30 min and then stirred at RT overnight. The reaction mixture is quenched with H20 (50 mL) and then concentrated in vacuo. The residue is triturated with saturated aqueous NH4C1 solution. The solid is collected by filtration, rinsed with ethyl acetate, and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde (E-3).

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, 22276-95-5, 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; INTELLIKINE, INC.; INFINITY PHARMACEUTICALS, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; CASTRO, Alfredo, C.; EVANS, Catherine, A.; WO2011/146882; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22276-95-5, 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. 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

METHOD L; 7-Benzenesulfonyl-5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine; [0192] To a slurry of the product from Method K (4.1 g/0.018 mol) in DMF (15 mL) and cooled to 0[deg.] C. was added 1.0 g (0.025 mol) of 60% sodium hydride in mineral oil and the resulting mixture stirred at 0[deg.] C. for 15 minutes. Benzenesulfonyl chloride (3.2 g/0.018 mol) was added, the reaction mixture warmed to room temperature and stirred for 2 hours. Water was then added (15 mL) and the resulting solid removed by filtration and dried in vacuo affording 5.9 grams (89%) of the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22276-95-5, its application will become more common.

Reference:
Patent; Pfizer Inc.; US6635762; (2003); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22276-95-5, 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]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, Product Details of 22276-95-5, blongs to pyrimidines compound. Product Details of 22276-95-5

General procedure: N,O-Bis(trimethylsilyl)acetamide (488.2 mg, 586.8 muL, 2.40 mmol) was added to a suspension of 7-bromo-6-chloro-7-deazapurine (464.9 mg, 2.00 mmol) in 20 mL dry acetonitrile. Afterwards, the solution was stirred for 15 min at room temperature in an argon atmosphere,followed by the addition of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-Dribofuranose(1.21 g, 2.40 mmol) and trimethylsilyl trifluoromethanesulfonate(533.4 mg, 434.4 muL, 2.40 mmol). The reaction mixture was heated for 2 h at 80 C under argon with vigorous stirring. After glycosylation, the solution was left to cool down and diluted with 400 mL ethyl acetate. The organic phase was sequentially washed twice with a saturated sodium hydrogen carbonate solution and brine. Subsequently, the organic layer was dried with magnesium sulfate and the solvent was removed under vacuum, to afford the crude nucleoside. Purification by column chromatography on silica gel with hexane/ethylacetate (2:1) as eluent yielded the product as colorless solid (864.0 mg,1.28 mmol, 64%). 1H NMR (300 MHz, DMSO-d6) delta 8.62 (1H, s), 8.32(1H, s), 8.00-7.84 (6H, m), 7.69-7.61 (3H, m), 7.54-7.40 (6H, m), 6.73(1H, d, J=5.0 Hz), 6.32-6.28 (1H, m), 6.16-6.11 (1H, m), 4.90-4.85(1H, m), 4.84-4.65 (2H, m); 13C NMR (75 MHz, DMSO-d6) delta 165.4,164.7, 164.5, 151.4, 151.0, 150.3, 134.0, 133.9, 133.6, 129.4, 129.4,129.3, 129.2, 129.2, 128.8, 128.6, 128.2, 114.9, 88.1, 86.6, 79.3, 73.5,70.6, 63.4; HRMS (ESI): m/z calcd for C32H24BrClN3O7 [M+H]+676.0481, found 676.0489.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22276-95-5, 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Lelle, Marco; Otte, Maik; Thon, Susanne; Bertinetti, Daniela; Herberg, Friedrich W.; Benndorf, Klaus; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1704 – 1713;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22276-95-5, 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]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, Recommanded Product: 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine, blongs to pyrimidines compound. Recommanded Product: 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

General Procedure 7 Step 2: Methyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate; To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (15 g, 64.377 mmol) in THF (378 ml.) n-BuLi (1.4 M in hexanes, 96.56 ml_, 135.19 mmol) is added dropwise at -78 0C. The reaction solution is stirred for 30 min and then methyl chloroformate (4.73 ml_, 61.15 mmol) in THF is added at -78 0C and the reaction mixture is allowed to attain room temperature and is stirred for 3 h. The reaction is quenched with aq. NH4CI. The solvent is distilled off and the residual solution is extracted with EtOAc (3 x 300 ml_). The combined organic layer is washed with water (300 ml_), brine (300 ml_), dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue is purified by column chromatography to give methyl 4-chloro-7H- pyrrolo[2,3-d]pyrimidine-5-carboxylate as a pale yellow solid.1H-NMR (400 MHz, DMSO-d6): delta 13.3 (brs, 1 H), 8.69 (s, 1 H), 8.42 (s, 1 H), 3.82 (s, 1 H). ESI- MS (pos.): 21 1.8 (M+H).

The synthetic route of 22276-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHEN, Yen Liang; DURAISWAMY, Jeyaraj; HALLER, Sarah; KEIM, Matthias; KONDREDDI, Ravinder Reddy; YIN, Zheng; WO2010/15643; (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. 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Safety of 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-i Jpyrimidine (40.0 g, 173 mmol) in dry tetrahydrofuran (700 mL) at -78 C was added rc-butyl lithium (195 mL, 2.5 M solution in hexane, 487 mmol) over the period of 2 hours. The reaction mixture was stirred for another 30 minutes at -78 C, after which ethyl chloroformate (17.8 mL, 186mmol) was added over 30 minutes. The reaction mixture was stirred for 2 hours at -60 C and then the temperature was slowly increased to 30 C. The reaction mixture was allowed to stir for 12 hours at 30 C. The progress of the reaction was monitored by TLC using 25% ethyl acetate in petroleum ether using iodine and 254 nm UV light to visualize the spot. The reaction mixture was then quenched with saturated solution of ammonium chloride (200 mL) at 0 C and the reaction mixture was extracted with ethyl acetate (*3). The combined organic layers were washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford a crude reaction mixture. The residue was purified by chromatography on silica eluting with 5-100% ethyl acetate/petroleum ether to afford ethyl 4-chloro-7H-pyrrolo[2,3-i ]pyrimidine-5- carboxylate as pale yellow solid. LRMS (ESI) calc’d for C9H7C1N302 [M-H]+: 224; found 224. 1H NMR (400 MHz, DMSO-D6): delta 13.28 (s, 1H), 8.70 (s, 1H), 8.39 (s, 1H), 4.31 (q, J= 7.2, 6.8 Hz, 2H), 1.34 (t, J= 7.6, 6.8 Hz, 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, 22276-95-5, 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; AHEARN, Sean, P.; CHRISTOPHER, Matthew; JUNG, Joon; PU, Qinglin; RIVKIN, Alexey; SCOTT, Mark, E.; WITTER, David, J.; WOO, Hyun Chong; CASH, Brandon; DINSMORE, Christopher; GUERIN, David; WO2013/85802; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22276-95-5, 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 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

1,1-dimethylethyl 3-(5-bromo-4-chloro-7H-pyrrolo(2,3-d]pyrimidin-7-yl)-1-azetidine carboxyla teTo a solution of 5-bromo-4-chloro-1 H-pyrrolo[2,3-d]pyrimidine (400 mg, 1 .721 mmol), 1 , 1- dimethylethyl 3-hydroxy-1 -azetidinecarboxylate (894 mg, 5.16 mmol) and triphenylphosphine (903 mg, 3.44 mmol) in Tetrahydrofuran (THF) (10 mL) was added dropwise DEAD (545 muIota, 3.44 mmol). The solution was let stir at room temp. After 1 hr the reaction observed 10% product and the reaction was heated at 60C. After 1 hr observed 80% desired product. Additional 100mg of the 5-bromo-4-chloro-1 H-pyrrolo[2,3- d]pyrimidine was added and heating was continued. The reaction was concentrated then loaded on to a 25g SNAP column with 0 to 35% EtOAc in Hexane gradient over 30minut.es to give 1 , 1-dimethylethyl 3-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)- 1-azetidinecarboxylate (624 mg, 94 % yield) as a white solid. LC-MS(ES) m/z = 386.9, 389.1 [M+H]+. 1 H NMR (400 MHz, DMSO-d6) delta 8.69 (s, 1 H), 8.38 (s, 1 H), 5.53 – 5.62 (m, 1 H), 4.33 (d, J = 8.34 Hz, 4H), 1 .43 (s, 9H).

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 22276-95-5, 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22276-95-5, 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. 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

To a mixture of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (G-1) (6.24 g, 26.8 mmol, 1.0 eq) in anhydrous THF (100 mL) at -78 C. under argon, n-BuLi solution (2.5 M in THF, 23.6 mL, 59.0 mmol, 2.2 eq) is added dropwise over 30 min. The reaction mixture is stirred at -78 C. for 1 h and then dry ice (300 g) is added in portions under an argon atmosphere. The resulting mixture is allowed to warm to RT and then stirred at RT overnight. The reaction mixture is diluted with H2O (200 mL) and extracted with ethyl acetate (50 mL*4). The aqueous layer is acidified with conc. HCl to adjust the pH to 3-4. The precipitate is collected by filtration, rinsed with H2O (30 mL) and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (H-1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22276-95-5, its application will become more common.

Reference:
Patent; Ren, Pingda; Liu, Yi; Li, Liansheng; Chan, Katrina; Wilson, Troy Edward; Castro, Alfredo C.; Evans, Catherine A.; Snyder, Daniel A.; US2012/122838; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 22276-95-5 , The common heterocyclic compound, 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3BrClN3, 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-bromo-4-cUoro-7H-pyrrolo[2 -d]pyrirnidine D3 (l.OOg) inDMF (10 mL) at 0 C was added sodium hydride (0.224 g, 5.59 mmol) and the mixture stirred for 20 minutes, Benzenesulfonyl chloride (0.66 mL, 5.16 mmol) was then added dropwise and the reaction mixture stirred in the cool bath for 1 hour. The mixture was poured onto water (140 mL) and the precipitate filtered, washed with water and dried in a vacuum oven to give D5 (1.60 g) as an off white solid, lH NMR (CDC13) delta 8.77 (1H, s), 8.23 (2H, dd), 7.85 (1H, s), 7.70 (1H, m), 7.59 (2H, ddd), MS(ES+) 372 [M(Ci2H779Br35Cl 302S)+H]+. The crude product was used without further purification into the preparation of D6..

The synthetic route of 22276-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONVERGENCE PHARMACEUTICALS LIMITED; WITTY, David R.; NORTON, David; TIERNEY, Jason Paul; LORTHIOIR, Ghislaine; SIME, Mairi; PHILPOTT, Karen Louise; WO2012/80735; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

A solution of 56b (20 g, 86 mmoi) in thy ACN (300 mL) under nitrogen was charged with iV,O-Bistrimethyisiiyi)acetamide (19.3 g, 95 mmol) then stirred at RT for 30 mm. The mixture was then charged with I -O-acetvl-2.3.5-tri-O-benzoyl-13-d-ribofiiranose (56c) (48.1 g, 78 mmol) and TMSOTf(21 g, 78 mmol) and stirred at RT for 30 mm. The mixture was then heated and stirred at 80 C for 5 h. The reaction mixture was cooled to RI, diluted with EtOAc (1 IL) washed with sat. sodium bicarbonate (ilL), brine (1 IL), dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure and purified by FCC (Si02, 15% EtOAc in hexanes) to afford 56d (31.4 g, 40.1 mmol, 51% yield) as a white solid foam. LCMS purity:86.5%; LRMS (ES1) m/z caicd for [M+H]?: 676.05/678.05. Found: 676.05/678.05.

With the rapid development of chemical substances, we look forward to future research findings about 22276-95-5.

Reference:
Patent; PRELUDE THERAPEUTICS, INCORPORATED; LUENGO, Juan; LEAL, Raul, A.; LIN, Hong; SHETTY, Rupa; (166 pag.)WO2018/85833; (2018); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C6H3BrClN3

To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (obtained in Reference Example 8(1); 2.00 g) in tetrahydrofuran (50 mL) was added dropwise under nitrogen atmosphere at -65C 2.64M butyllithium-hexane solution (7.2 mL), and then the mixture was stirred for 30 minutes. To the reaction mixture was added a solution of ethyl chloroformate (905 muL) in tetrahydrofuran (5 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and then the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (solvent; hexane/ethyl acetate = 65/35 to 20/80) to give 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid ethyl ester (1.43 g) as a colorless solid (yield: 74%). MS(APCI)m/z; 226/228[M+H]+.

The synthetic route of 22276-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP2390254; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia