Category: 941685-26-3

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. 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., name: 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

0.2g of compound 2 and 0.11g of 4-aminopyrazole were dissolved in n-butanol. 0.27g of N,N-diisopropylethylamine was added to the solution and was heated at 150C under microwave for 2h. After completion of the reaction, the solvent was evaporated to dryness using a rotary evaporator under reduced pressure to obtain a crude product. The product was purified by column chromatography (dichloromethane:methanol = 20:1) to give 0.15g of compound 3 as a yellow solid, yield: 65%.

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, 941685-26-3, 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Shandong University; Zhang, Yingjie; Xu, Wenfang; Liang, Xuewu; (24 pag.)CN105418616; (2016); A;,
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 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C12H18ClN3OSi

A 1000 mL round bottom flask was charged with 4-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (10.00 g, 35.23 mmol), 1-butanol (25.0 mL), 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (15.66 g, 52.85 mmol), water (25.0 mL) and potassium carbonate (12.17 g, 88.08 mmol). This solution was degased 4 times, filling with nitrogen each time. To the solution was added tetrakis(triphenylphosphine)palladium(0) (4.071 g, 3.523 mmol). The solution was degased 4 times, filling with nitrogen each time. The mixture was stirred overnight at 100 C. After being cooled to room temperature, the mixture was filtered through a bed of celite and the celite was rinsed with ethyl acetate (42 mL). The filtrate was combined, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The organic extracts were combined and concentrated under vacuum with a bath temperature of 30-70 C. to give the final compound 4-(1H-pyrazol-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine. Yield: 78%. LC-MS: 316.2 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 941685-26-3.

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

Synthetic Route of 941685-26-3 ,Some common heterocyclic compound, 941685-26-3, molecular formula is C12H18ClN3OSi, 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.

Step 1: 4-methyl-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine 103.6 g of 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine and 2.96 g of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium were added to 1.13 L of tetrahydrofuran, and cooled down to -15?-5 C., and then 200 mL of methylmagnesium bromide (3M dissolved in ether) was slowly added dropwise thereto. After the addition was completed, the resulting mixture was heated to 60?65 C. and reacted under reflux for 2 hours. After the reaction was completed, the temperature was lowered to -15?-5 C., and then the reaction was quenched by slowly dropwise adding 455 mL of a saturated ammonium chloride solution. The resulting mixture was filtered, the filter cake was rinsed with 455 mL of tetrahydrofuran, and then the filter cake was discarded, and the filtrate was concentrated under reduced pressure. To the residue was added 455 mL of purified water, and 1.13 L of ethyl acetate was added to extract the resulting mixture twice. The organic phases were combined and washed with 150 g of saturated brine. Then, the organic phase was concentrated under reduced pressure to distill off the solvent to obtain 103.2 g 4-methyl-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. 1H-NMR (500 MHz, DMSO-d6): delta=8.67 (s, 1H), 7.63 (d, J=3.7 Hz, 1H), 6.70 (d, J=3.6 Hz, 1H), 5.60 (s, 2H), 3.54?3.45 (m, 2H), 2.64 (s, 3H), 0.81 (t, J=8.0 Hz, 2H), 0.12 (s, 9H); MS (ES): 264.15 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,941685-26-3, its application will become more common.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; Zhang, Xiquan; Zhang, Aiming; Zhou, Zhou; Yang, Leilei; Yao, Huadong; Zhu, Xueyan; Wang, Hubo; (29 pag.)US2019/23712; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 941685-26-3, 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. 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

233 mg (0. 82mmo 1) 2- [(4-chloropyrrolo [2,3 -d]pyrimidin-7-yl)methoxy] ethyl-trimethylsilane was dissolved in 4 ml dry THF and cooled down to -78 C and 500 jiL (1.8 M stocksolution, 0.9 mmol, 1.1 eq.) LDA was added. The mixture was stirred under nitrogen for40 minutes at -78 C then 208 mg iodine (0.82 mmol, 1 eq.) was added and allowed to warm to r.t. It was stirred for 40 minutes, then water was added. The solution was extracted with EEO (2 x 15 ml), combined organic phase was dried (magnesium sulfate) and evaporated. The residue was purified by flash chromatography (Eluent: heptane-EEOgradient).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,941685-26-3, 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; KOTSCHY, Andras; WEBER, Csaba; VASAS, Attila; MOLNAR, Balazs; KISS, Arpad; MACIAS, Alba; MURRAY, James Brooke; LEWKOWICZ, Elodie; GENESTE, Olivier; CHANRION, Maia; DEMARLES, Didier; (105 pag.)WO2017/212012; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 941685-26-3, 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. 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

To the quenched reaction mixture, which contains crude 4-chloro-7-[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (15, 18.63 g, 65.64 mmol) from previous reaction as described above, was added 1,2-dimethoxyethane (DME, 38 mL), powder potassium carbonate (K2CO3, 23.56 g, 170.5 mmol, 2.6 equiv), 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (3, 18.60 g, 69.89 mmol, 1.06 equiv) at room temperature. The resulting mixture was degassed four times backfilling with nitrogen gas each time before being treated with tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4, 244.2 mg, 0.21 mmol, 0.003 equiv) at room temperature. The resulting reaction mixture was degassed four times backfilling with nitrogen gas each time before being warmed to 80 C. for 4-8 h. When TLC and HPLC showed that the reaction was deemed complete, the reaction mixture was gradually cooled to room temperature and filtered through a short bed of Celite (10 g). The Celite bed was washed with ethyl acetate (EtOAc, 20 mL). The two layers of the filtrate were separated, and the aqueous layer was extracted with ethyl acetate (EtOAc, 2¡Á30 mL). The combined organic extracts were washed with saturated aqueous NaCl solution (20 mL), dried over magnesium sulfate (MgSO4), and concentrated under reduced pressure. The residue, which contains the crude desired Suzuki coupling product (16), was then transferred to a 500 mL round bottom flask with THF (22 mL) for subsequent de-protection reaction without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,941685-26-3, 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Zhou, Jiacheng; Liu, Pingli; Lin, Qiyan; Metcalf, Brian W.; Meloni, David; Pan, Yongchun; Xia, Michael; Li, Mei; Yue, Tai-Yuen; Rodgers, James D.; Wang, Haisheng; US2010/190981; (2010); A1;,
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. 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. Formula: C12H18ClN3OSi

Step 1: 4-chloro-6-methyl-7-{[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3d]pyrimidine To a stirred solution of Intermediate 2a (100 mg, 0.352 mmol) in THF (1 mL) was added LDA (2.0M; 0.19 mL, 0.39 mmol) dropwise at -78 C. The reaction mixture was stirred at this temperature for 40 minutes, then MeI (0.11 mL, 1.8 mmol) was added and the reaction was stirred at -78 C for an additional 40 minutes before being quenched with EtOAc and poured into a mixture of EtOAc and silica gel. The resulting mixture was concentrated in vacuo to afford a crude solid that was purified by column chromatography on silica gel, eluting with EtOAc/hexane (2-20%) to afford the desired product as a colorless oil. LRMS calc’d for C13H21ClN3OSi [M+H]+, 298; found 298. 1H NMR (500 MHz, CDCl3) delta 8.60 (s, 1H), 6.40 (s, 1H), 5.65 (s, 2H), 3.51 (t, 2H), 2.56 (s, 3H), 0.90 (t, 2H), 0.06 (s, 9H).

The synthetic route of 941685-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; GUERIN, David Joseph; BRUBAKER, Jason, D.; MARTINEZ, Michelle; JUNG, Joon, O.; ANTHONY, Neville, J.; SCOTT, Mark, E.; HOFFMAN, Dawn Marie Mampreian; WOO, Hyun Chong; DINSMORE, Christopher, J.; (75 pag.)EP2629777; (2018); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia