Category: 3680-69-1

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.

To a solution of 4-chloropyrrolo[2,3-d]pyrimidine (200 g, 1.3 mol, 1.0 eq.) in N,N-dimethylformamide was added 60% NaH (62.4 g, 1.56 mol, 1.2 eq.) in an ice bath, and stirred for 1 hour at room temperature after completion of addition. 2-(Trimethylsilyl)ethoxymethyl chloride (SEMCl, 260 g, 1.56 mol, 1.2 eq.) was slowly added drop-wise under cooling in an ice bath. After completion of addition, the reaction was stirred for 1 hour in an ice bath, quenched with water, and extracted with ethyl acetate. The combined organic phase was washed with a saturated brine solution, dried over anhydrous sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure to obtain residue, which was purified by column chromatography on silica gel to afford 4-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (2) (312.2 g, yield: 91.8%). 1H-NMR (500 MHz, CDCl3): delta 8.64 (s, 1H), 7.38 (d, J=3.6 Hz, 1H), 6.65 (d, J=3.6 Hz, 1H), 5.64 (s, 2H), 3.52 (t, J=8.2 Hz, 2H), 0.90 (t, J=8.2 Hz, 2H), -0.07 (s, 9H); HRMS (ESI) calcd. for C12H18N3OSi [M+H]+ 284.0980; Found: 284.0995.

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; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; CENTAURUS BIOPHARMA CO., LTD.; ZHANG, Xiquan; Zhang, Aiming; Zhou, Zhou; Yao, Huadong; Xie, Jie; (32 pag.)US2019/211021; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application 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.

Under ice-cooling conditions, 2.0g of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine was dissolved in 50mL N,N-dimethylacetamide. 0.58g of NaH was added dropwise to the solution and stirred for 15 minutes. 2.2g of 2-chloromethoxyethyl trimethylsilane was added and the reaction was continued maintaining the temperature at 5C for 4h. The solution was then quenched with saturated ammonium chloride solution. The aqueous phase was extracted with ethyl acetate. The organic phase was washed with water. Each 100mL saline solution was washed three times. The organic phase was dried over anhydrous magnesium sulfate overnight. The mixture was filtered and the solvent was distilled off under reduced pressure to give a crude product. The product was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 50:1) to give 2.6g of intermediate 2 as a colorless liquid, yield: 70%.

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; Shandong University; Zhang, Yingjie; Xu, Wenfang; Liang, Xuewu; (24 pag.)CN105418616; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application 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.

Under ice-cooling conditions, 2.0g of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine was dissolved in 50mL N,N-dimethylacetamide. 0.58g of NaH was added dropwise to the solution and stirred for 15 minutes. 2.2g of 2-chloromethoxyethyl trimethylsilane was added and the reaction was continued maintaining the temperature at 5C for 4h. The solution was then quenched with saturated ammonium chloride solution. The aqueous phase was extracted with ethyl acetate. The organic phase was washed with water. Each 100mL saline solution was washed three times. The organic phase was dried over anhydrous magnesium sulfate overnight. The mixture was filtered and the solvent was distilled off under reduced pressure to give a crude product. The product was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 50:1) to give 2.6g of intermediate 2 as a colorless liquid, yield: 70%.

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; Shandong University; Zhang, Yingjie; Xu, Wenfang; Liang, Xuewu; (24 pag.)CN105418616; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3680-69-1, 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. 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, 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.

Into a round bottom flask the catalyst PdCl2(dppf), under an atmosphere of nitrogen, was placed with 15 mL of toluene along with a stir bar. A suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 1.47 g, 9.57 mmol) in 15 mL of toluene was added at room temperature. After stirring for 10 minutes, methylmagnesium bromide (17.00 mL, 3.00 M in ether, 51.00 mmol) was added dropwise. The solution turned from orange to yellow, and was slowly heated to 60 C. and stirred for 3 hrs at 60 C. and then overnight at room temperature. The resulting dark orange reaction mixture was quenched with 1 N hydrochloric acid and adjusted to pH~5, then extracted with ethyl acetate and water saturated with sodium chloride. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluding with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a yellow solid (42, 202 mg). 1H-NMR(dmso-d6) was consistent with the desired compound. MS(ESI) [M+H+]+=134.3.

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; Plexxikon, Inc.; US2009/286783; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application 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 4-chloro-7H-pyrrolo[2,3-d] pyrimidine (15.4 g,0.100 mol) in tetrahydrofuran, 60% sodium hydride (8.0 g, 0.200 mol)was added in batches under ice bath. The reaction mixture was stirredunder ice bath for 0.5 h, and then chloromethyl pivalate (30.1 g,0.200 mol) was added to the mixture. Subsequently, the reaction wasstirred at room temperature for 1.5 h. After completed, the mixture waspoured into saturated ammonium chloride solution. The mixture wasextracted with ethyl acetate (50 ml×5), the organic layer was washedwith brine, dried over anhydrous Na2SO4, and then filtered and concentratedto yield 4 as a yellow solid (27.5 g, 85.0%). MS (ESI) m/z:268.4 [M+H]+

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; Jiang, Feng; Zang, Linghe; Miao, Xiuqi; Jia, Fang; Wang, Jie; Zhu, Minglin; Gong, Ping; Jiang, Nan; Zhai, Xin; Bioorganic and Medicinal Chemistry; vol. 27; 18; (2019); p. 4089 – 4100;,
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.

A mixture of compound Int-4-1 (14.5 g, 94.42 mmol, 1 eq.) and Selectfluor (50.17 g, 141.63 mmol, 1.5 eq.) was addedACN (725 mE),AcOH (152.25 g, 2.54 mol, 145 mE, 26.85 eq.) and degassed and purged with N2 for 3 times, and then the mixture was stirred at 70 C. for 16 hr under N2 atmosphere. ECMS showed no compound Int-4-1 was remained. Several new peaks were shown on ECMS and 45% of desired compound was detected. The reaction mixture was concentrated under reduced pressure to remove solvent. The residue was diluted with toluene (200 mE) and concentrated under reduced pressure to remove solvent twice. The residue was purified by column chromatography (Si02, petroleum ether/ethyl acetate=30/1 to 8/1) to give compound Int-4 (10 g, 54.46 mmol, 57.68% yield, ECMS purity 93.43%) as a yellow solid. ?H NMR (400 MHz, DMSO-d5) oe ppm 12.49 (br s, 1H) 8.55-8.67 (m, 1H) 7.71 (t, J=2.63 Hz, 1H); ECMS: (M+Hj: 171.9.

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; Prelude Therapeutics, Incorporated; Lin, Hong; Luengo, Juan; Shetty, Rupa; Hawkins, Michael; (96 pag.)US2019/48014; (2019); A1;,
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 suspension of sodium hydride (36.141 g, 903.62 mmol) in N,N-dimethylacetamide (118 mL) at -5 C. (ice/salt bath) was added a dark solution of 4-chloropyrrolo[2,3-d]pyrimidine (119.37 g, 777.30 mmol) in N,N-dimethylacetamide (237 mL) slowly. The flask and addition funnel were rinsed with N,N-dimethylacetamide (30 mL). A large amount of gas was evolved immediately. The mixture became a slightly cloudy orange mixture. The mixture was stirred at 0 C. for 60 min to give a light brown turbid mixture. To the mixture was slowly added [2-(trimethylsilyl)ethoxy]methyl chloride (152.40 g, 914.11 mmol) and the reaction was stirred at 0 C. for 1 h. The reaction was quenched by addition of 12 mL of H2O slowly. More water (120 mL) was added followed by methyl tert-butyl ether (MTBE) (120 mL). The mixture was stirred for 10 min. The organic layer was separated. The aqueous layer was extracted with another portion of MTBE (120 mL). The organic extracts were combined, washed with brine (120 mL×2) and concentrated under reduced pressure to give the crude product 4-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine as a dark oil. Yield: 85.07 g (97%); LC-MS: 284.1 (M+H)+. It was carried to the next reaction without purification.

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; Huang, Taisheng; Xue, Chu-Biao; Wang, Anlai; Kong, Ling Quan; Ye, Hai Fen; Yao, Wenqing; Rodgers, James D.; Shepard, Stacey; Wang, Haisheng; Shao, Lixin; Li, Hui-Yin; Li, Qun; US2011/224190; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature 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.

To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (8 g, 52.3 mmol) in CH2Cl2 (200 ml) was added NIS (14 g, 62.5 ml). The mixture was stirred at rt for 5 h. LC- MS indicated complete reaction. The mixture was filtered and the filtered solid was washed with CH2Cl2 (50 ml), followed by hot water (500 ml). The solid was then dried in vacuum oven at 40 C for 2 days to give 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine, MM as a gray solid (13.6 g, 93%). 1H NMR (DMSO-d6) delta 12.97 (br s, 1H), 8.60 (s, 1H), 7.95 (s, 1H). LC/MS m/z 279.9 (M+H).

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

Application of 3680-69-1, 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. 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, 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.

Step 1To a solution of 4-chloro-7H-pyrro]o[2,3-d]pyrimidine (8.0 g , 52.32 mmol, 1.0 eq) in DMF (40 raL), NiS ( 15.7g , 57.55 mmol, 1.1 eq) was added at 0 C. The reaction mixture was stirred overnight at room temperature. Water (40 rnL) was added to the reaction mixture, extracted with EtOAc. The organic layer was dried over Na2S04 and concentrated under vacuum to give 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (14.6 g, 100 % in yield).

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; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David Michael; BRAMELD, Kenneth Albert; WO2012/158795; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route 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.

METHOD L 7-Benzyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidine To a stirred solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (250 mg/1.63 mmol) in 12 mL of DMF was added 676 mg (4.89 mmol) of potassium carbonate and the resulting mixture stirred at room temperature for 20 min. Benzylchloride (310 mg/2.45 mmol) was added and the new mixture stirred at room temperature for 24 h then filtered, concentrated and the residue purified by silica gel chromatography (3:1 hexanes/ethyl acetate) affording 318 mg (80%) of the title compound. LRMS: 244.1 (M+1).

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 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Blumenkopf, Todd A.; Flanagan, Mark E.; Brown, Matthew F.; Changelian, Paul S.; US2002/19526; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia