Category: 26452-81-3

Adding a certain compound to certain chemical reactions, such as: 26452-81-3, 4-Chloro-6-methoxypyrimidine, 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, HPLC of Formula: C5H5ClN2O, blongs to pyrimidines compound. HPLC of Formula: C5H5ClN2O

10761] Under nitrogen atmosphere, the compound Cl (500 mg, 3.46 mmol was dissolved in DME (10 mE). 2-chloro- 3-(trifluoromethyl)phenyl boronic acid (1.164 g, 5.19 mmol), 2 mol/L aqueous solution of sodium carbonate (5.19 mE, 10.38 mmol) and PdC12 (dppf)(282 mg, 0.346 mmol) were added to the solution. The mixture was stirred at 90° C. for 1 hour. After cooled to room temperature, water was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed by brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by colunm chromatography (chloroform-methanol) to afford the compound C2 (600 mg, yield 60percent).10762] MS (mlz): 289 [(M+H)]

The synthetic route of 26452-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIONOGI & CO., LTD.; TANAKA, Satoru; OGAWA, Tomoyuki; OGATA, Yuki; FUJITA, Masahide; (89 pag.)US2016/318916; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 26452-81-3 , The common heterocyclic compound, 26452-81-3, name is 4-Chloro-6-methoxypyrimidine, molecular formula is C5H5ClN2O, 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.

ARBF containing 4-chloro-6-methoxy pyrimidine (3.13 g, 21.62 mmol), 4- chloro-2-(tetramethyl- 1,3 ,2-dioxaborolan-2-yl) aniline (7.31 g, 21.62 mmol), Na2CO3 (2.29 g, 21.62 mmol), DME (86 ml), EtOH (10.81 ml) and water (10.81 ml) was equipped with a condenser. The mixture was purged with Ar for several mm thenPd(dppf)C12.CH2C12 adduct (1.77 g, 2.16 mmol) was added. The reaction was heated at90 °C for 5 h. The reaction was cooled to rt, diluted with water and extracted withEtOAc. The organic layer was washed with brine, concentrated and purified by normalphase chromatography to give 4-chloro-2-(6-methoxypyrimidin-4-yl)aniline (2.86 g, 56.1percent yield) as yellow solid. MS (ESI) m/z. 236.0 (M+H)t ?H NMR (500MHz, CDC13) oe8.78 (d, J=1.1 Hz, 1H), 7.49 (d, J=2.5 Hz, 1H), 7.15 (dd, J=8.8, 2.5 Hz, 1H), 6.99 (d, J=1.1 Hz, 1H), 6.67 (d, J=8.8 Hz, 1H), 5.89 (br. s., 2H), 4.03 (s, 3H).

The synthetic route of 26452-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMITH II, Leon M.; PINTO, Donald J. P.; CORTE, James R.; EWING, William R.; (163 pag.)WO2016/205482; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 26452-81-3, name is 4-Chloro-6-methoxypyrimidine, molecular formula is C5H5ClN2O, 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. Application In Synthesis of 4-Chloro-6-methoxypyrimidine

4-Chloro-6-methoxypyrimidine (0.562 g, 3.89 mmol), 6-chloro-4-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 H-benzo [d]imidazole (0.722 g, 2.59 mmol) and 2aqNa2CO3 (0.549 g, 5.18 mmol) in DME (20.74 mL), EtOH (2.59 mL) was purged with Ar for several mm. Then PdC12(dppf)-CH2Cl2Adduct (0.2 12 g, 0.259 mmol) was added and heated to 90 °C. After 2 h, the reaction was cooled to rt, diluted with waterand extracted with EtOAc. The organic layer washed with brine, dried over Na2 SO4, filtered, and concentrated to give a brown oil. The crude material was purified by normal phase chromatography using EtOAc and MeOH as eluants to give 6-chloro-4-(6- methoxypyrimidin-4-yl)-1H-benzo[d]imidazole (148 mg, 22percent). MS(ESI) m/z: 261.1 (M+H) and 263.1 (M+2+H). ?H NMR (500MHz, DMSO-d6) oe 8.93 (d, J1.1 Hz, 1H),8.42 (s, 1H), 8.36 (br. s., 1H), 8.20 (d, J=1.9 Hz, 1H), 7.84 (s, 1H), 4.02 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 26452-81-3.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 26452-81-3, 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 26452-81-3 as follows.

To a RBF equipped with a reflux condenser containing DME (42.9 mL), EtOH(5.36 mL) was added 4-chloro-6-methoxypyrimidine (1.55 g, 10.72 mmol), 4-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.5 g, 10.72 mmol) and 2 M aqNa2CO3 (5.36 mL, 10.72 mmol). The mixture was purged with Ar for 10 mm thenPdC12(dppf)-CH2Cl2Adduct (0.876 g, 1.072 mmol) was added and the reaction mixtureheated at 90 ¡ãC. After 2 h, the reaction was diluted with water and extracted with EtOAc. The organic layer washed with brine and concentrated to give a brown oil. The crude product was purified by normal phase chromatography using heptane and EtOAc as eluents to give 2-(6-methoxypyrimidin-4-yl)-4-methylaniline (670 mg, 29percent) as a solid.MS(ESI)m/z: 216.1 (M+H). ?HNMR(500MHz, CDC13-d) oe 8.79 (d, J1.1 Hz, 1H),7.33 (d, J1.4 Hz, 1H), 7.08 – 7.01 (m, 2H), 6.67 (d, J8.3 Hz, 1H), 5.68 (br. s., 2H), 4.03 (s, 3H), 2.29 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26452-81-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 26452-81-3 , The common heterocyclic compound, 26452-81-3, name is 4-Chloro-6-methoxypyrimidine, molecular formula is C5H5ClN2O, 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 mixture of methyl 3-ethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (10520 mg, 30 mmol), 4-chloro-6-methoxypyrimidine (4645 mg, 31.5 mmol), dichloro(1,V-bis(diphenylphosphino) ferrocene) palladium (II) dichloromethane adduct) (2449 mg, 3 mmol) and potassium phosphate tribasic monohydrate (20719 mg, 90 mmol) in water (4 mL) and DMF (150 mL) is degassed for 20 min under a nitrogen stream, then stirred at RT for 1 h15. The RM is filtered through celite, the filtrate is concentrated under vacuum, the residue is partitioned between water and EtOAc. The organic layer is further washed with brine, dried over MgS04, filtered and concentrated. Purification by FC (heptane/EtOAc, from 1 :0 to 0:1) affords the title compound as a yellow solid (7.87 g, 89percent). LC-MS B: tR = 0.93 min; [M+H]+ = 295.18.

The synthetic route of 26452-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; BOSS, Christoph; CORMINBOEUF, Olivier; FRETZ, Heinz; LYOTHIER, Isabelle; POZZI, Davide; RICHARD-BILDSTEIN, Sylvia; SIENDT, Herve; SIFFERLEN, Thierry; (190 pag.)WO2018/210987; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 26452-81-3, 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 26452-81-3 as follows.

A mixture of methyl 3-ethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (10520 mg, 30 mmol), 4-chloro-6-methoxypyrimidine (4645 mg, 31.5 mmol), Pd(dppf)Cl2-DCM (2449 mg, 3 mmol) and potassium phosphate tribasic monohydrate (20719 mg, 90 mmol) in water (4 mL) and DMF (150 mL) is degassed for 20 min under a nitrogen stream, then stirred at RT for 1 h 15. The RM is filtered through celite, the filtrate is concentrated under vacuum, the residue is partitioned between water and EtOAc. The organic layer is further washed with brine, dried over MgS04, filtered and concentrated. Purification by FC (heptane/EtOAc, from 1 :0 to 0:1) afforded the title compound as a yellow solid (7.87 g, 89percent). LC-MS A: tR = 0.93 min; [M+H]+ = 295.18.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26452-81-3, its application will become more common.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; BOSS, Christoph; CORMINBOEUF, Olivier; FRETZ, Heinz; LYOTHIER, Isabelle; POZZI, Davide; RICHARD-BILDSTEIN, Sylvia; SIENDT, Herve; SIFFERLEN, Thierry; (223 pag.)WO2018/210994; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 26452-81-3, 4-Chloro-6-methoxypyrimidine, 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, Computed Properties of C5H5ClN2O, blongs to pyrimidines compound. Computed Properties of C5H5ClN2O

General procedure: To a 5 mL vial containing a stir bar, 3-(2-aminopyrimidin-5-yl)-6-cyclobutyl-2-fluorophenol (88 mg, 0.34 mmol) and 4-amino-6-chloropyrimidine (46 mg, 0.36 mmol) were added K2CO3 (70 mg, mg, 0.51 mmol), 18-crown-6 (9 mg, 0.03 mmol) and DMA (0.68 mL). The resultant mixture was stirred at 120¡ã Celsius for approximately 3 hours before cooling to room temperature and passing it through a syringe filter and subjecting the filtrate to FCC to afford the title compound (42 mg, 35percent). The title compound was prepared using conditions similar to those described in Example 164 heating for 3 hours at 120¡ã Celsius using Intermediate G and 6-chloro-4-pyrimidinyl methyl ether giving title compound and Example 205. MS (ESI): mass calcd. for C19H20FN5O2, 369.16; m/z found, 370.1 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.46-8.42 (m, 1H), 8.08 (d, J=1.5, 1H), 7.98 (s, 1H), 7.78-7.69 (m, 1H), 7.32-7.27 (m, 1H), 5.90 (s, 1H), 4.67 (s, 2H), 3.51 (s, 3H), 1.37 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,26452-81-3, 4-Chloro-6-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2014/221310; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 26452-81-3, 4-Chloro-6-methoxypyrimidine, 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, Product Details of 26452-81-3, blongs to pyrimidines compound. Product Details of 26452-81-3

General procedure: Compound 5b (284 mg, 0.58 mmol), bromobenzene (0.08 mL, 0.75 mmol), and Pd(PPh3)2Cl2 (40 mg, 0.06 mmol)were added to a flask containing a magnetic stir with EtOH (5.80 mL). Triethylamine (0.18 mL, 1.28 mmol) was then added to the reaction mixture and the reaction mixture was stirred under reflux condition for 10 h under a N2 atmosphere. After cooling the mixture to room temperature, solvent was removed in vacuo. The crude material was diluted with ethyl acetate (5.00 mL) and water (5.00 mL). The aqueous layer was separated from the organic layer, and the aqueous layer was extracted with ethyl acetate (2 ¡Á 15 mL). Organic layers were then combined, washed with brine solution, and dried with MgSO4, and solvent was removed in vacuo. The crude material was then purified by flash column chromatography on silica gel using n-hexane/ethyl acetate = 1:1 as the eluent to give the desired product 8a as a white solid (m.p. 180 ¡ãC) in 57percent yield (146 mg); white solid; 1H-NMR (Bruker AC-600 FT-NMR spectrometer at 600 MHz, CD3OD-d4) delta ppm 7.47?7.19 (m, 12H), 7.07 (s, 1H), 6.96(d, J = 7.8 Hz, 1H), 6.15 (s, 0.77H), 5.68 (br, 0.23H), 4.75 (q, J1 = 115.8, J2 = 18.0, 2H), 3.65 (m, 1H),2.11 (s, 3H), 1.82?1.08 (m, 10H); 13C-NMR (Bruker AC-600 FT-NMR spectrometer at 150.9 MHz, CD3OD-d4) delta ppm 175.41, 171.51, 142.75, 142.33, 140.03, 136.65, 131.20, 130.26, 130.00, 129.93,129.72, 128.56, 128.15, 126.67, 126.21, 125.77, 63.73, 51.35, 50.19, 33.63. 26.75, 26.25, 26.20, 22.72; HRMS (ESI, positive ion) (m/z): [M+H]+ calcd for C29H32N2O2, 441.2543; found, 441.2542.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,26452-81-3, 4-Chloro-6-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Chung, Sheng-Hsuan; Lin, Ting-Ju; Hu, Qian-Yu; Tsai, Chia-Hua; Pan, Po-Shen; Molecules; vol. 18; 10; (2013); p. 12346 – 12367;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia