Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 1780-26-3, 2-Methyl-4,6-dichloropyrimidine, 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, Quality Control of 2-Methyl-4,6-dichloropyrimidine, blongs to pyrimidines compound. Quality Control of 2-Methyl-4,6-dichloropyrimidine

The crude 2-methyl-4,6-dichloropyrimidine (41.8 g.; 256 mmol) was dissolved in dichloromethane (200 mL) and chilled to -78C in an inert atmosphere. Morpholine (48 g.; 550 mol) dissolved in dichloromethane (100 mL) was added slowly. The reaction was allowed to warm to room temperature while stirring overnight. The organic layer was washed with saturated ammonium chloride (2×100 mL), dried with sodium sulfate, and evaporated to give 2-methyl-4-chloro-6-morpholino-pyrimidine (48.5 g.; 227 mmol).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1780-26-3, 2-Methyl-4,6-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2006/124662; (2006); A1;,
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Pyrimidine – Wikipedia

Reference of 262353-34-4 , The common heterocyclic compound, 262353-34-4, name is 2,4-Diiodopyrimidine, molecular formula is C4H2I2N2, 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.

General procedure: Compound 4 (1equiv per iodine atom), NEt3 (0.5mL), CuI (6mol%), and Pd(PPh3)2Cl2 (6mol%) were added to iododiazine (1mmol) in THF (5mL). The suspension was stirred at room temperature overnight under nitrogen atmosphere. The suspension was then diluted with a mixture of water and dichloromethane (1:1, 20mL) and the organic layer separated. The aqueous layer was extracted with dichloromethane (2¡Á20mL). The combined organic extracts were dried over MgSO4, filtered, and evaporated.

The synthetic route of 262353-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gauthier, Sebastien; Vologdin, Nikolay; Achelle, Sylvain; Barsella, Alberto; Caro, Bertrand; Robin-Le Guen, Francoise; Tetrahedron; vol. 69; 39; (2013); p. 8392 – 8399;,
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Application of 720-01-4, 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. 720-01-4, name is Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate, molecular formula is C8H6ClF3N2O2, 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.

A solution of P(t-Bu)3 (0.32 g, 1.57 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (0.72 g, 0.78 mmol), in 10 ml of THF, stirred at room temperature for 30 min, the dark red heterogeneous solution Pd(P(t-Bu)3)2 formed. Then KF (2.74 g, 47.24 mmol), and 3,4-dimethoxyphenylboronicacid (2.15 g, 11.80 mmol) in dry THF (50ml) was added. Finally ethyl-4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate (2g, 7.87 mmol), was added under N2 atmosphere. The reaction mixture was heated to 65C for 14 h. TLC showed the completion of the reaction. Then the mixture was cooled and concentrated under vacuo to get crude residue, which was purified by column chromatography over silica gel (Ethylacetate/ Hexane, 1:3) to afford title product as an off-white solid in 74% yield. ESI-MS: 357 (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 720-01-4, Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate.

Reference:
Article; Purushothaman, Baskaran; Arumugam, Parthasarathy; Kulsi, Goutam; Song, Joon Myong; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 673 – 690;,
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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;,
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Electric Literature of 17321-93-6 ,Some common heterocyclic compound, 17321-93-6, molecular formula is C5H6BrN3, 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.

General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 molpercent) and further degassed (5times). The resulting mixture was stirred at 95 ¡ãC under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100percent) to yield the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17321-93-6, its application will become more common.

Reference:
Article; Akhter, Sundus; Lund, Bjarte Aarmo; Ismael, Aya; Langer, Manuel; Isaksson, Johan; Christopeit, Tony; Leiros, Hanna-Kirsti S.; Bayer, Annette; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 634 – 648;,
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Reference of 374930-88-8 , The common heterocyclic compound, 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, molecular formula is C13H19BrN4O2, 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.

Tri-isopropyl borate (1.18 g, 6.25 mmol) was added, dropwise to a magnetically stirred solution of 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (1.72 g, 5.00 mmol) in THF (15 mL). The mixture was cooled to -70 oC and butyl lithium (3.91 mL, 6.25 mmol) was added, dropwise maintaining the temperature at -60 oC over 15 minutes. The mixture was then warmed to -20 oC over 20 minutes followed by the addition of acetic acid (0.501 mL, 8.75 mmol). The reaction mixture was then evaporated and the resultant residue suspended in methanol (2 mL) and water (15 mL) to which hydrogen peroxide (0.870 mL of a 35% w/v solution in water, 49.4 mmol) was introduced, dropwise with vigorous stirring. The reaction was stirred for 18 hours and the resultant precipitate was filtered and washed with water. The solid was partitioned between dichloromethane and water and the separated organic phase was dried (MgSO4), filtered and concentrated to yield tert-butyl 4-(5-hydroxypyrimidin-2-yl)piperazine-1-carboxylate (1.32 g, 92%) as a white solid, NMR Spectrum: (DMSOd6) 1.46 (s, 9H), 3.43 (m, 4H), 3.61 (m, 4H), 8.09 (S, 2H), 9.30 (s, 1H); Mass Spectrum: M+H+ 281.

The synthetic route of 374930-88-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; De Savi, Chris; Waterson, David; Pape, Andrew; Lamont, Scott; Hadley, Elma; Mills, Mark; Page, Ken M.; Bowyer, Jonathan; Maciewicz, Rose A.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 16; (2013); p. 4705 – 4712;,
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Pyrimidine – Wikipedia

Reference of 13162-26-0, Adding some certain compound to certain chemical reactions, such as: 13162-26-0, name is 2,4-Dichloro-6-methyl-5-nitropyrimidine,molecular formula is C5H3Cl2N3O2, 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 13162-26-0.

A-40. Methyl N-(2-chloro-6-methyl-5-nitropyrimidin-4-yl)-N-methyl-L-alaninate A solution of 2,4-Dichloro-6-methyl-5-nitro-pyrimidine (1.86 g, 8.96 mmol) in 20 ml of acetone was added dropwise to a mixture of methyl (2S)-2-(methylamino)propanoate (1 g, 8.54 mmol) and potassium carbonate (1.77 g, 12.8 mmol) in acetone and water. The reaction was stirred at room temperature for 16 hours. The mixture was evaporated in vacuo and the residue was taken into a water and extracted with ethyl acetate (3*75 ml). The combined extracts were combined, washed with brine, dried over sodium sulfate, filtered, and evaporated in vacuo to afford the title product as a viscous yellow oil, wt. 1.54 g (62.5% yield). 1H NMR (300 MHz, CDCl3) delta 5.34 (q, J=7.3 Hz, 1H), 3.78 (s, 3H), 2.88 (s, 3H), 2.48 (s, 3H), 1.57 (d, J=7.3 Hz, 3H).

According to the analysis of related databases, 13162-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Lauffer, David J.; Bemis, Guy; Boyd, Michael; Deininger, David; Deng, Hongbo; Dorsch, Warren; Gu, Wenxin; Hoover, Russell R.; Johnson, JR., Mac Arthur; Ledeboer, Mark Willem; Ledford, Brian; Maltais, Francois; Penney, Marina; Takemoto, Darin; Waal, Nathan D.; Weng, Tiansheng; (667 pag.)US2019/322673; (2019); A1;,
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Application of 13544-44-0, Adding some certain compound to certain chemical reactions, such as: 13544-44-0, name is 2,4-Dichloro-5-iodopyrimidine,molecular formula is C4HCl2IN2, 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 13544-44-0.

12) (2-chloro-5-iodopyrimidine-4-yl)-(3-morpholin-4-yl-propyl)-amine:; In accordance with procedure 2, 3-morpholin-4-yl-propylamine (0.73 ml, 5 mmol) and N-ethyldiisopropylamine (1.71 ml, 10 mmol) are dissolved in 100 ml acetonitrile under argon and cooled to -35C. The solution of 2,4-dichloro-5- iodo-pyrimidine (1.37, 5.0 mmol) in 50 ml acetonitrile is then added dropwise at-35C internal temperature. Stirred 1 hr further at -30 to -20 0C, then slowly warmed up to RT and stirred for 3 days at RT.The reaction mixture is concentrated on the rotary evaporator. The residue is treated with 200 ml ethyl acetate and 75 ml sat. NaHCO3 soln., well shaken and the aqueous phase further extracted 2 x with 75 ml portions of ethyl acetate. The ethyl acetate phase is dried over Na2SO4 dried, filtered, concentrated and the residue dried at the oil pump: 1.92 g colourless and crystalline crude product.The crude product is purified by column chromatography (5Og column, mobile phase: gradient hexane: ethyl acetate 80% to 100% ethyl acetate): 1.66 g(97%).1H-NMR (400 MHz, DMSO-D6): delta 1.66 (m, 2H), 2.30 (m, 6H), 3.37 (m, 2H), 3.57(m, 4H)1 7.42 (t, 1 H), 8.27 (s, 1 H).MS: 383 (MH+).

According to the analysis of related databases, 13544-44-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING AKTIENGESELLSCHAFT; WO2007/71455; (2007); A1;,
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Pyrimidine – Wikipedia

Application of 1240390-28-6, 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.1240390-28-6, name is 2,4-Dichloropyrimidine-5-carboxylic acid amide, molecular formula is C5H3Cl2N3O, molecular weight is 192.0028, as common compound, the synthetic route is as follows.

4-(tert-Butylamino)-2-chloropyrimidine-5-carboxamide A mixture of 2,4-dichloro-pyrimidine-5-carboxamide (10.0 g), DIPEA (11 mL) in NMP (30 mL) were stirred at 25 C. tert-Butylamine (6.6 mL) was charged to the mixture, and the mixture was stirred at 25 C. for 16 h. Water (100 mL) was added to the mixture at 25 C. The mixture was stirred for 1 h. The suspension was filtered, washed with water (50 mL) and dried in a vacuum oven at 40 C. with a nitrogen bleed for 24 h to give 4-(tert-butylamino)-2-chloropyrimidine-5-carboxamide as a white solid (8.7 g, 84%). 1H NMR (DMSO-d6) delta 9.41 (s, 1H), 8.55 (s, 1H), 8.19 (s, 1H), 7.67 (s, 1H), 1.42 (s, 9H).

Statistics shows that 1240390-28-6 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloropyrimidine-5-carboxylic acid amide.

Reference:
Patent; Ferretti, Antonio Christian; Man, Hon-Wah; Muslehiddinoglu, Jale; Xu, Jean; Yong, Kelvin Hin-Yeong; Beauchamps, Marie Georges; Kothare, Mohit Atul; Zou, Nanfei; Boersen, Nathan Andrew; Li, Ying; Ye, Ying; US2015/210650; (2015); A1;,
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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;,
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