Category: 582313-57-3

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 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 582313-57-3

To a solution of trans-4-(dimethylamino)cyclohexan-l-ol (280 mg, 1.95 mmol, 3.90 equiv) in tetrahydrofuran (5 mL) was added sodium hydride (200 mg, 5.00 mmol, 9.97 equiv, 60percent). The mixture was stirred at 0°C for 30 min. Then 4-chloro-5-fluoro-7H-pyrrolo[2,3- d]pyrimidine (86 mg, 0.50 mmol, 1.00 equiv) was added. The resulting solution was stirred for 16 h at 70°C. The resulting solution was extracted with 5×15 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product (70 mg) was purified by Prep-HPLC with the following conditions: Column, SunFire Prep CI 8, 19* 150mm 5um; mobile phase, Water with 50mmol NH4HCO3 and CH3CN (5.0percent CH3CN up to 25.0percent in 10 min, up to 95.0percent in 2 min,down to 5.0percent in 2 min); Detector, uv 254/220nm. This resulted in 31 mg (22percent) of trans-4-([5-fluoro-7H-pyrrolo[2,3- d]pyrimidin-4-yl]oxy)-N,N-dimethylcyclohexan-l -amine as a off-white solid. LC-MS: (ES,m/z): 279 [M+H] + 1H NMR (300 MHz, CD3OD, ppm): delta 1.64-1.38 (m, 4H), 1.99-2.07 (m, 2H), 2.25- 2.40 (m, 9H), 5.16-5.20 (m, 1H), 6.96 (d, 1H), 8.25 (s, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 582313-57-3.

Reference:
Patent; NIMBUS IRIS, INC.; HARRIMAN, Geraldine C.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; WESSEL, Matthew David; GREENWOOD, Jeremy Robert; WO2014/11911; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 582313-57-3, 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. 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3ClFN3, 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.

Vial A: Add to dry round bottom flask (purged by N2)(S,S)-DACH-naphthyltrozine ligand (1.13 g, 1.43 mmol) andPd2(dba)3.CHCl3 (493 mg, 0.48 mmol).The vial was purged four times with N2 and added DCE (50 mL,Sprayed by N2 for 30 minutes). The black solution was stirred for 30 minutes at 12°C,A red-brown solution was obtained at this time.Vial B: To dry round bottom flask(by N2 purification) BB-1 (7155 mg, 23.82 mmol) was added,4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (4.5 g, 26.23 mmol) andCs2 CO3 (8.54 g, 26.2 mmol). The vial was purged with N2 five times and DCE (50 mL) was added followed by addition of the contents of vial A via syringe.The reaction was stirred at 12 °C under N2 for 24 hours. The reaction mixture was filtered and concentrated to a brown gum. The crude residue was purified by flash biotage (120 g, tannin, EtOAc/petroleum ether = 15percent) to give NN-1 (6.4 g, 76percent) as an off-white solid.

According to the analysis of related databases, 582313-57-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; KUMPF, ROBERT ARNOLD; MCALPINE, INDRAWAN JAMES; MCTIGUE, MICHELE ANN; PATMAN, RYAN; RUI, EUGENE YUANJIN; TATLOCK, JOHN HOWARD; TRAN-DUBE, MICHELLE BICH; WYTHES, MARTIN JAMES; (445 pag.)TW2018/2074; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 582313-57-3, Adding some certain compound to certain chemical reactions, such as: 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H3ClFN3, 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 582313-57-3.

To containCCl4 (5 mL, 51 mmol)Add hexamethylphosphoramide to a solution of 5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-ribose (9.13 g, 30 mmol) in toluene (100 mL) 7.2 mL, 40 mmol). After stirring at 0 C for 2.5 hours,The reaction mixture was added to 4-chloro-5-fluoro-7H-pyrrole [2,3-d]pyrimidine (14-1, 3.1 g,20 mmol), a solution of tris(3,6-dioxaheptyl)amine (TDA-1) (3 mL, 9 mmol) and KOH (2.6 g, 4.5 mmol) in toluene (100 mL)The entire reaction mixture was stirred at room temperature for 24 hours.The reaction was terminated by the addition of a saturated aqueous solution of NH 4 Cl.Transfer the entire mixture to a separatory funnel. The aqueous layer is extracted with AcOEt.The combined organic layers were washed with brine.Dry (Na2SO4)Concentration in vacuo gave the crude product 17-2.

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. 582313-57-3, 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Hongyi Biological Technology Co., Ltd.; Wu Rongguang; Yi Dewu; (140 pag.)CN109694397; (2019); A;,
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. 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 582313-57-3

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (700 mg, 4.08 mmol, 1.00 equiv) in tetrahydrofuran (40 mL), then compound 24a (1.528 g, 4.08 mmol, 1.00 equiv, J. Org. Chem. 2009, 74, 6819-6824) and triphenylphosphine (3.208 g, 12.24 mmol, 3.00 equiv) was added sequentially. This was followed by the addition of a solution of DEAD (2.131 g, 12.25 mmol, 3.00 equiv) in tetrahydrofuran (20 mL) dropwise with stirring at room temperature. The resulting solution was allowed to stir for 3 hours at room temperature,and then it was concentrated in vacuo. The resulting residue was purified using flash column chromatography on silica gel, eluting with ethyl acetate/petroleum ether (1:8) to provide 300 mg (14percent) of compound 24b as a white solid.

The synthetic route of 582313-57-3 has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 582313-57-3 ,Some common heterocyclic compound, 582313-57-3, molecular formula is C6H3ClFN3, 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 stirred solution of (3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2- dimethyl-3a,6a-dihydro-4H-cyclo penta[d] [l,3]dioxol-4-ol (3.5 g, 8.24 mmol) in THF (50 ml) was added 4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (3.54 g, 20.61 mmol, which was synthesized by following the same reaction protocol as was described in WO2005/16878, A2), triphenylphosphine (5.40 g, 20.61 mmol), DIAD (4.01 ml, 20.61 mmol) at 0C and stirred for 30 min. The resulting reaction mixture was stirred at 25C for l6h. Volatiles were removed in vacuo and the crude residue was purified by combiflash (0550) (Rf200, Teledyne/Isco) instrument onto a redisep Rf column with gradient elution (0 to 10%) of ethyl acetate in petroleum ether to afford the title compound (2.7g, 56.7%) as an off-white solid. LCMS m/z = 577.94 (M+; 100%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,582313-57-3, its application will become more common.

Reference:
Patent; LUPIN LIMITED; NAIR, Prathap, Sreedharan; GUDADE, Ganesh, Bhausaheb; SETHI, Sachin; LAGAD, Dipak, Raychand; PAWAR, Chetan, Sanjay; TRYAMBAKE, Mahadeo, Bhaskar; KULKARNI, Chaitanya, Prabhakar; HAJARE, Anil, Kashiram; GORE, Balasaheb, Arjun; KULKARNI, Sanjeev, Anant; SINDKHEDKAR, Milind, Dattatraya; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; (241 pag.)WO2019/116302; (2019); 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. 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Recommanded Product: 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine

4.1.11 7-(2-O-Acetyl-3,5-di-O-benzyl-4-C-methyl-beta-d-ribofuranosyl)-4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (12) To a slurry of 4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine 11 (2.06 g, 12 mmol) in dry MeCN (20 ml) was added N,O-bis(trimethylsilyl)acetamide [BSA] (2.94 ml, 9.55 mmol) and the mixture was stirred at rt for 15 min (clear solution). Then a solution of 1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-methyl-beta-d-ribofuranose 5 (5.14 g, 12 mmol) in MeCN (40 ml) was added, followed by TMSOTf (4.34 ml, 24 mmol). The solution was stirred at 80 ¡ãC for 3 h. After cooling, the mixture was diluted with EtOAc (200 ml), cautiously washed with saturated aq NaHCO3 (100 ml) and aqueous phase was re-extracted with EtOAc (2 * 25 ml). Combined organic phases were dried (MgSO4), concentrated in vacuo and loaded on silica by co-evaporation. Column chromatography (SiO2, hexane-AcOEt, 10:1) afforded nucleoside 12 as yellowish oil (3.76 g, 58percent). 1H NMR (500 MHz, CDCl3): 1.32 (s, 3H, CH3-4′); 2.05 (s, 3H, CH3CO); 3.40 (d, 1H, Jgem = 10.2 Hz, H-5’a); 3.56 (d, 1H, Jgem = 10.2 Hz, H-5’b); 4.42 (d, 1H, J3′,2′ = 5.7 Hz, H-3′); 4.48 (bd, 1H, Jgem = 11.5 Hz, CH2a-Bn-5′); 4.50 (d, 1H, Jgem = 11.5 Hz, CH2a-Bn-3′); 4.56 (d, 1H, Jgem = 11.5 Hz, CH2b-Bn-5′); 4.60 (d, 1H, Jgem = 11.6 Hz, CH2b-Bn-3′); 5.56 (bt, 1H, J2′,3′ = J2′,1′ = 5.3 Hz, H-2′); 6.62 (dd, 1H, J1′,2′ = 5.0 Hz, J1′,F = 1.8 Hz, H-1′); 7.29-7.41 (m, 11H, H-o,m,p-Bn-3′,5′, H-6); 8.59 (s, 1H, H-2). 13C NMR (125.7 MHz, CDCl3): 18.99 (CH3-4′); 20.69 (CH3CO); 73.64 (CH2-Bn-5′); 74.18 (CH2-Bn-3′); 74.43 (CH2-5′); 75.97 (CH-2′); 77.79 (CH-3′); 85.00 (CH-1′); 86.30 (C-4′); 107.58 (d, JC,F = 14.4 Hz, C-4a); 109.64 (d, JC,F = 27.0 Hz, CH-6); 127.86 and 127.97 (CH-o-Bn-3′,5′); 128.03 and 128.11 (CH-p-Bn-3′,5′); 128.45 and 128.62 (CH-m-Bn-3′,5′); 137.21 (C-i-Bn-5′); 137.57 (C-i-Bn-3′); 141.60(d, JC,F = 253.6 Hz, C-5); 147.04 (d, JC,F = 1.2 Hz, C-7a); 150.46 (d, JC,F = 3.7 Hz, C-4); 151.50 (CH-2); 169.93 (CO). 19F NMR (470.3 MHz, DMSO-d6): -167.38 (s, 1F, F-5). IR (ATR): nu 1678, 1622, 1593, 1457, 1231, 1070, 1028, 741, 700 cm-1. MS (ESI) m/z 540 (M+H), 562 (M+Na). HRMS (ESI) for C28H27O5N3ClFNa [M+Na] calcd: 562.15155; found: 562.15140.

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, 582313-57-3, 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Article; Nau?, Petr; Caletkova, Olga; Perlikova, Pavla; Po?tova Slav?tinska, Lenka; Tlou??ova, Eva; Hodek, Jan; Weber, Jan; D?ubak, Petr; Hajduch, Marian; Hocek, Michal; Bioorganic and Medicinal Chemistry; vol. 23; 23; (2015); p. 7422 – 7438;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 582313-57-3, 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 582313-57-3 as follows.

This compound is synthesized using a procedure such as that described by ?.Vorbruggen and U. Niedballa in J. Org. Chem., 39: 3654-3660 (1974). The 4-chloro-5-fluoro-7H- pyrrolo[2,3-d]pyrimidine (1?) used in this transformation is prepared following the procedure described by A. B. Eldrup, et al. in J. Med. Chem.. 47: 5284 (2004).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,582313-57-3, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2006/65335; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia