Category: 175791-49-8

Application of 175791-49-8, 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. 175791-49-8, name is 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4BrN3, 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 dried tetrahydrofuran (20 mL) was added 5-bromo-7H-pyrrolo[2,3-d]pyrimidine (1.00 g, 5.05 mmol) . Sodium hydride (404 mg, 10.10 mmol, 60mass) was added to the solution at 0, and the resulting mixture was stirred at 0 for 30 min. Then p-toluenesulfonyl chloride (1.16 g, 6.06 mmol) was added to the mixture, and the mixture was warmed to rt and stirred overnight. The reaction was quenched with water (100 mL) , and the aqueous layer was extracted with ethyl acetate (100 mL × 3) . The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dry and the residue was purified by silica gel column chromatography (n-hexane/EtOAc (v/v) 5/1) to give the title compound as a yellow solid (1.40 g, 79 %) . MS (ESI, pos. ion) m/z: 351.9 [M+H]+ 1H NMR (400 MHz, CDCl3) delta (ppm) : 9.08 (s, 1H) , 8.92 (s, 1H) , 8.12 (d, J 8.3 Hz, 2H) , 7.80 (s, 1H) , 7.35 (d, J 8.1 Hz, 2H) , 2.43 (s, 3H) .

According to the analysis of related databases, 175791-49-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; ZHANG, Yingjun; (161 pag.)WO2018/41091; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 175791-49-8, 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. 175791-49-8, name is 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4BrN3, 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.

Description 2; Ethyl (5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)acetate (D2)5-Bromo-7H-pyrrolo[2,3-d]pyrimidine (D1 , 123 mg, 0.621 mmol) was dissolved in tetrahydrofuran (3 ml_), cooled in an ice bath and treated with sodium hydride (60% by weight, 27.3 mg, 0.683 mmol) portionwise under argon. The resulting mixture was stirred for 15 minutes, allowed to warm to room temperature and stirred for 45 minutes. Ethyl bromoacetate (0.069 ml_, 0.621 mmol) was added and the resulting mixture was stirred for 30 minutes. The solvent was removed under reduced pressure. The residue taken up in water, neutralised using saturated ammonium chloride and extracted with ethyl acetate (x 3). The ethyl acetate layers were combined, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography eluting with 1 :1 ethyl acetate/iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a white solid. LC/MS (ES+ve): [M+H]+ at m/z 284, 286 (Ci0H10BrN3O2 requires [M+H]+ at m/z 284, 286).

According to the analysis of related databases, 175791-49-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/80682; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 175791-49-8 , The common heterocyclic compound, 175791-49-8, name is 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4BrN3, 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-7H-pyrrolo[2,3-d]pyrimidine (1, 0.9 g, 4.54 mmol) in tetrahydrofuran (10 mL) at 0 C., was added sodium hydride (0.27 g, 6.81 mmol, 60% in hexane). The reaction mixture was allowed to stir at 0 C. for 20 min. Chloromethyl 2-trimethylsilylethyl ether (0.9 g, 5.44 mmol) was then added and the reaction mixture was stirred at 0 C. for an additional 30 min., and then quenched with water. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using 5% methanol in dichloromethane to afford 5-bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (2). Yield: 1.3 g, 86%; MS (ESI) m/z 328[M+1]+.

The synthetic route of 175791-49-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); 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 175791-49-8, name is 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine

[00303] Step 1: Synthesis of 5-bromo-7-(methylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine. To a solution of 5-bromo-7H-pyrrolo[2,3-d]pyrimidine (or any other suitable aromatic halide, 1 mmol) in DMF (5 mL) was added NaH (43 mg, 60%, 1.1 mmol) at 0oC, After 5 min., MsCl* (114 mg, 1.0 mmol) was added and the mixture was stirred at 0oC for 1h. The mixture was diluted with EtOAc (20 mL), successively washed with water (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by chromatographic column on silicagel to give 5-bromo-7-(methylsulfonyl)- 7H- pyrrolo[2,3-d]pyrimidine (265 mg, 95% yield). ESI- LCMS (m/z): 275.9 [M+1]+.[00304] *Alternatively, other alkylating, acylating, carbamoylating, or sulfonylating agents can be employed is similar manner.

With the rapid development of chemical substances, we look forward to future research findings about 175791-49-8.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; MORADEI, Oscar, Miguel; SHAPIRO, Gideon; JIN, Lei; BABINE, Robert, E.; (495 pag.)WO2016/44641; (2016); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 175791-49-8, 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 175791-49-8, name is 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 5-bromo-7H-pyrrolo[2,3-d]pyrimidine (12.8 g, 55.11 mmol) in THF was added NaH (4.48 g, 112.01 mmol) portion wise at 0C. under nitrogen. The resulting mixture was stirred at 5 C. for 1 hour then p-toluenesulfonyl chloride (11.6 g, 60.85 mmol) was added portion wise. The reaction mixture was allowed to warm to 20 C. and stirred for 3 hours. The reaction mixture was poured into a mixture of ice and 1M aq. HCl while stirring. The mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, the solids were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by crystallization from ethyl acetate to afford 2, 5-bromo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine as white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 2.36 (s, 3H), 7.47 (d, J=8.0 Hz, 2H), 8.06 (d, J=8.0 Hz, 2H), 8.31 (s, 1H), 9.03 (s, 1H), 9.06 (s, 1H). LC-MS ES+ m/z=351.8; Rt: 1.16 min, method D.

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 175791-49-8, 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Janssen Sciences Ireland UC; JONCKERS, Tim Hugo Maria; MC GOWAN, David Craig; RABOISSON, Pierre Jean-Marie Bernard; EMBRECHTS, Werner Constant Johan; GUILLEMONT, Jerome Emile Georges; (42 pag.)US2017/253600; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia