Category: 3680-69-1

Synthetic Route of 3680-69-1, Adding some certain compound to certain chemical reactions, such as: 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H4ClN3, 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 3680-69-1.

In a 3L round bottom flask, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (92 g, 600 mmol) was suspended in 1600 mL dichloromethane; NBS (108 g, 600 mmol) was gradually added and the mixture was stirred at room temperature for 1 hr. An additional amount of NBS (20 g, 56 mmol) was added and the mixture was stirred at room temperature for 2 hours. The resulting solid was collected via filtration, rinsed with dichloromethane and dried. The solid was triturated with 2 L of water for 2 hours and the solid was collected via filtration; The solid was dried under a vacuum to a constant weight (112 g, 80%). 1H NMR (DMSO-de) delta 8.68 (s, 1H), 7.99 (s, 1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHIMERIX, INC.; ALMOND, Merrick; LANIER, Ernest, Randall; MUSSO, David, Lee; WARE, Roy; WO2010/135520; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3680-69-1, 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.3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

To a suspension of commercial 4-chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75 g (70.00 mmol) in 150mL DCM, and added 1-bromopyrrolidine-2,5-dione (18.69 g, 105.00 mmol) at ambient temperature overnight. Upon the reaction completion, large amounts of precipitates formed. The precipitates were collected by filtration, and the filtrate was removed under reduced pressure to get the solid, washed with DCM, to yield of the title compound as yellow solid (15.00 g, 92% yield). 1H NMR (400 MHz, DMSO) delta 12.97(s, 1H), 8.63 (s, 1H), 7.95 (d, J 2.6 Hz, 1H).

Statistics shows that 3680-69-1 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Article; Zhang, Chufeng; Pei, Heying; He, Jun; Zhu, Jiali; Li, Weimin; Niu, Ting; Xiang, Mingli; Chen, Lijuan; European Journal of Medicinal Chemistry; vol. 169; (2019); p. 121 – 143;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3680-69-1, 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.3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

Compound 13a (5.0 g, 32.56 mmol, 1.00 equiv) was taken up in DMF 60 mL. and to the resulting solution was added N-iodosuccinimide (7.3 g, 32.45 mmol, 1.00 equiv) in portions at room temperature. The resulting reaction was allowed to stir for 2 hours at room temperature, and then was concentrated in vacuo. The resulting residue was purified using flash column chromatography on silica gel and eluted with ethyl acetate/petroleum ether (1:3) to provide 6.7 g (74%) of compound 13b as a white solid.

Statistics shows that 3680-69-1 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; VERMA, Vishal; ARASAPPAN, Ashok; NJOROGE, F. George; GIRIJAVALLABHAN, Vinay; BOGEN, Stephane, L.; DANG, Qun; OLSEN, David, B.; WO2013/9735; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3680-69-1, 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 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Step 1. 4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (Compound 3) 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75 g (70 mmol) (Toronto Research Chemicals, Inc) and N-iodosuccinimide (16.8 g, 75 mmol) were dissolved in 400 mL of dry DMF and left at ambient temperature in the darkness over night. The solvent was evaporated. The yellow residue was suspended in hot 10% solution of Na2SO3, filtered, washed twice with hot water and crystallized from ethanol to yield 14.6 g (74.6%) of the title compound as off-white crystals. The mother liquid was evaporated up to 1/3 volume and crystallized again from ethanol to give 2.47 g (12.3%) of the title product; Total yield is close to 100%; M.p. 212-214 (decomposition); UV lambdamax: 307, 266, 230, 227 nm (methanol); MS: 277.93 (M-H), 313 (M+Cl); 1H-NMR (DMSO-d6): 12.94 (s, 1H, NH), 8.58 (s, 1H, H-2), 7.94 (s, 1H, H-8).

According to the analysis of related databases, 3680-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genelabs Technologies, Inc.; US2005/215510; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3680-69-1 ,Some common heterocyclic compound, 3680-69-1, molecular formula is C6H4ClN3, 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.

4-chloro-7H-pyrrolo[2,3-d]pyrimidine (2-E, 20.0 g, 130.7 mmol) dissolved in DCM (800 mL) was treated portion-wise with N-bromosuccinimide (26.7 g, 149.8 mmol), while maintaining the temperature around 25-30 C. The reaction mixture was stirred at room temperature overnight. Water was added (500 mL) and the phases were separated. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was triturated in Et2O affording after filtration 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine as a white solid (2-F, 22.43 g, 74%). M.p.: 242-244 C.; NMR (400 MHz, DMSO-d6) delta 12.96 (s, 1H), 8.61 (s, 1H), 7.94 (s, 1H); MS m/z 232 [M(35Cl, 79Br)+H]+, 234 [M(35Cl, 81Br)+H]+, 234 [M(37Cl, 79Br)+H]+, 236 [M(37Cl, 81Br)+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3680-69-1, its application will become more common.

Reference:
Patent; ArQule, Inc.; Lapierre, Jean-Marc; Eathiraj, Sudharshan; Namdev, Nivedita; Schwartz, Brian; Ota, Yusuke; Momose, Takayuki; Tsunemi, Tomoyuki; Inagaki, Hiroaki; Nakayama, Kiyoshi; (18 pag.)US9630968; (2017); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3680-69-1 ,Some common heterocyclic compound, 3680-69-1, molecular formula is C6H4ClN3, 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 typical procedure for the preparation of 3a:2-bromopropane (74 mg, 0.6 mmol) was added to a solution of 1a (92 mg, 0.6 mmol) and K2CO3 (110 mg, 0.8 mmol) in 5 mL DMF at 70 C. According to TLC the reaction went to completion after 4 h. The mixture was extracted with ethyl acetate (3 * 10 mL). The combined organic layers were washed with brine(10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give the crude product 2a, which was added to a solution of amino-phenol(66 mg, 0.6 mmol) and Cs2CO3 (585 mg, 1.8 mmol) in 10 mL DMSO without further purification. After stirring for 6 h at 80 C, the mixture was cooled to room temperature and extracted with ethyl acetate (3 * 10 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give the crude product, which was further purified by column chromatography(petroleum ether/ethyl acetate 2:1) to afford compound 3a as a brown solid(121 mg, 75% over two steps).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Yang; Fang, Jianping; Cai, Haiyan; Xiao, Fei; Ding, Kan; Hu, Youhong; Bioorganic and Medicinal Chemistry; vol. 20; 18; (2012); p. 5473 – 5482;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3680-69-1 ,Some common heterocyclic compound, 3680-69-1, molecular formula is C6H4ClN3, 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 NaH (3 g, 0.13 mol) in DMF (60 mL)Suspension is slowSlow to join 1(10 g, 0.066 mol) in DMF (40 mL).The reaction mixture was stirred at 0 & lt; 0 & gt; CStirring for 2 hours,A light brown cloudy mixture was obtained.And then slowly added to the mixture2- (trimethylsilyl) ethoxymethyl chloride (SEMCl) (12.7 g, 0.08 mol)Stirred overnight at room temperature,The reaction was quenched with water and extracted with ethyl acetate,The filtrate was concentrated under reduced pressure. Purification by flash chromatography gave intermediate 2(15 g, 81%),As a pale yellow oil;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3680-69-1, its application will become more common.

Reference:
Patent; Hangzhou East China Pharmaceutical Group New Drug Institute Co., Ltd.; Yin Jianming; Lv Yubin; Li Bangliang; (18 pag.)CN106905322; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.Safety of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine

Synthesis of 7-(2-nitrobenzyloxy)methyl-7-deaza-2?-deoxyadenosine-5?-triphosphate6-Chloro-7-iodo-7-deazapurine (dA.23): Compound dA.23 was synthesized according to the procedure described by Ju et al. (2006, which is incorporated herein by reference). To a suspension of 6-chloro-7-deazapurine (1.00 g, 6.51 mmol) in anhydrous CH2Cl2 (55 mL) was added N-iodosuccinimide (1.70 g, 7.56 mmol). The reaction was protected from light while stirring at room temperature for two hours. The reaction was then concentrated down in vacuo. The material was re-crystallized from hot methanol to yield 6-chloro-7-iodo-7-deazapurine dA.23 (0.94 g, 52%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Lasergen, Inc.; Litosh, Vladislav A.; Hersh, Megan N.; Stupi, Brian P.; Wu, Weidong; Metzker, Michael L.; US9200319; (2015); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3680-69-1, Adding some certain compound to certain chemical reactions, such as: 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H4ClN3, 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 3680-69-1.

To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (2.6 g, 17.4 mmol) in DMF (50 mL) was added NIS (3.9 g, 17.4 mmol). The reaction was stirred at room temperature overnight. Water (125 mL) was added to the reaction mixture, and the precipitate was filtered and washed with water. The solid was dried in vacuo to afford the title compound. MS m/z 280.0 (M + H+) (Method M).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; IRM LLC; CHEN, Bei; FAIRHURST, Robin, Alec; FLOERSHEIMER, Andreas; FURET, Pascal; GUAGNANO, Vito; JIANG, Songchun; LU, Wenshuo; MARSILJE, Thomas, H.; MCCARTHY, Clive; MICHELLYS, Pierre-Yves; STAUFFER, Frederic; STUTZ, Stefan; VAUPEL, Andrea; WO2011/29915; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3680-69-1, 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 3680-69-1 as follows.

To a suspension of 4-Chloro-7H-pyrrolo [2,3-d] pyrimidine (2.5g, 16 mmol) in CDC13 (65 mL) was added NBS (2.9g, 16 mmol) and the reaction mixture stirred and heated at reflux for 2.5 hours. The mixture was cooled to room temperature, the solids isolated by vacuum filtration, rinsed with cold CHC13 and air dried to give 5-Bromo-4-chloro-7H- pyrrolo [2, 3-d] pyrimidine (3. 0g, 79%. ) LCMS (APCI+) m/z 232 and 234 [M+H] + ; Rt: 2.32 min. 1H NMR (DMSO-d6,400 MHz) 6 12. 98 (1H, br. s), 8.63 (1H, s), 7.96 (1H, s. )

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3680-69-1, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2005/51304; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia