Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 32779-38-7, 2-Chloro-5-iodopyrimidine, 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, COA of Formula: C4H2ClIN2, blongs to pyrimidines compound. COA of Formula: C4H2ClIN2

b) 2,5-dichloro-N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)benzenesulfonamide Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.56 g) was added to a solution of 2,5-dichloro-N-(3-ethynyl-2,4-difluorophenyl)benzenesulfonamide (3.0 g), 2-chloro-5-iodopyrimidine (2.6 g), DIPEA (3.0 mL) and copper(I) iodide (79 mg) in THF (50 mL) at room temperature. The mixture was stirred under a nitrogen atmosphere at room temperature for 16 hr. The reaction mixture was filtered through celite, and the filtrate was diluted with water and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (761 mg). 1H NMR (300 MHz, DMSO-d6) delta 7.22-7.32 (1H, m), 7.42 (1H, td, J=8.9, 5.9 Hz), 7.71-7.81 (2H, m), 7.87 (1H, dd, J=2.0, 0.8 Hz), 9.03 (2H, s), 10.83 (1H, s).

The synthetic route of 32779-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); A1;,
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Application of 38275-55-7, 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 38275-55-7 as follows.

Intermediate 5; l-(5-Fluoropyrimidin-2-yl)ethanoneTo a solution of 5-fluoropyrimidine-2-carbonitrile (Intermediate 4, 2.5 g) in Et2O (50 ml) at 00C was added drop-wise a solution of MeMgBr (12 ml, 3.0M in Et2O). The resulting solution was stirred at this temperature for 30 minutes, and was then allowed to warm to ambient temperature overnight. The mixture was quenched with a solution of saturated NH4Cl(aq) and extracted with Et2O. The organic extracts dried and evaporation gave a colored residue. Purification by column chromatography (ISCO, 3% MeOH/DCM) to afford the title compound (800 mg). 1H NMR (CDCl3) delta 8.75 (s, 2H), 2.77 (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,38275-55-7, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/7753; (2009); A2;,
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Application of 1059735-34-0, 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. 1059735-34-0, name is 7-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine, molecular formula is C14H13Cl2N3, 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 mixture of 7-benzyl-2,4-dichloro-6,8-dihydro-5H- pyrido [3,4-d]pyrimidine (10 g, 34.0 mmol), 2-piperazin-2-ylacetonitrile (10.1 g, 51.0 mmol, 2 HC1) and DIEA (17.6 g, 136 mmol, 23.7 mL) in dioxane (100 mL) was stirred at 50 C for 2 hours. B0C2O (14.8 g, 68.0 mmol, 15.6 mL) was added and the mixture was stirred at 50 C for 2 hours. The mixture was concentrated under vacuum and the residue was diluted with ethyl acetate (500 mL). The separated organic layer was washed with water (1 chi 300 mL), brine (1 chi 200 mL), dried over sodium sulfate, filtered and concentrated under vacuum. The residue was triturated with ethyl acetate (100 mL). The precipitate was filtered and the filtered cake was washed with ethyl acetate (50 mL) and dried under vacuum to give a gray solid. The filtrate was concentrated under vacuum. The residue was purified by column chromatography over silica gel (petroleum ether/ethyl acetate 100/1 to 1/2). The desired fractions were collected and concentrated under vacuum to give solid then combined with above solid to give tert-butyl 4-(7- benzyl-2-chloro-6,8-dihydro-5H-pyrido[3,4-Patent; MIRATI THERAPEUTICS, INC.; ARRAY BIOPHARMA, INC.; FISCHER, John, P.; FELL, Jay, Bradford; BLAKE, James, F.; HINKLIN, Ronald, Jay; MEJIA, Macedonio, J.; HICKEN, Erik, James; CHICARELLI, Mark, Joseph; GAUDINO, John, J.; VIGERS, Guy, P.A.; BURGESS, Laurence, E.; MARX, Matthew, Arnold; CHRISTENSEN, James, Gail; LEE, Matthew, Randolf; SAVECHENKOV, Pavel; ZECCA, Henry, J.; (529 pag.)WO2017/201161; (2017); A1;,
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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.776-53-4, name is Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate, molecular formula is C8H11N3O2S, molecular weight is 213.2568, as common compound, the synthetic route is as follows.Computed Properties of C8H11N3O2S

(3) To a suspension of the compound (2.52 g) obtained in (2) above in chloroform (70 ml) is added manganese dioxide powder (7.56 g), which is three-fold amount compared to the starting material, and the mixture is stirred vigorously at room temperature overnight. The insoluble substances are removed by filtration, and the filtrate is concentrated in vacuo to obtain a colorless solid, which is extremely insoluble in an organic solvent. The resultant solid is recrystallized from a mixed solution of chloroform and methanol, triturated with a mixed solvent of chloroform-diisopropyl ether-hexane, washed with diisopropyl ether and hexane to give 2-methylthio-5-formyl-4-aminopyrimidine (1.75 g) as colorless powder. M.p. 186-187 C, MS (m/z): 170 (MH+). IR(nujol): 3406, 3289, 3177, 1667, 1631, 1616, 1585, 1529, 1387, 1180, 781 cm-1 .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,776-53-4, Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1364950; (2003); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1161763-15-0, name is 4-Amino-6-bromo-2-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 4-Amino-6-bromo-2-methylpyrimidine

60% sodium hydride (12.0 g, 0.30 mol) was suspended in THF (300 mL) and cooled down to 0 C. 4-amino-6-bromo-2-methylpyrimidine (Compound 9) (18.7 g, 0.1 mol) was then added in batches and stirred for 30 min. After methyl 2-chlorothiazole-5-formate (Compound 10) (17.7 g, 0.1 mol) was added in batches, the reactants were heated and reacted by refluxing for 4 h, and then cooled down to room temperature for reaction overnight. When controlling the temperature between 0 C. and 5 C., hydrochloric acid (2N) was added for neutralization reaction. After adding keep heat and stirred to grow grains for 1 h. Filtrate and wash the cake with water, and then dry to give target Compound 11 (25.8 g, yield is 78.4%).[0177]Element analysis: C10H9BrN4O2S, Calculated: C, 36.49; H, 2.76; N, 17.02. Found: C, 36.51; H, 2.77; N, 16.99.[0178]1H-NMR (500 MHz, DMSO-d6): delta(ppm) 2.580 (s, 3H), 3.820 (s, 3H), 6.960 (S, 1H), 8.160 (s, 1H), 12.376 (s, 1H) (which disappeared after exchanging D2O)[0179]13C-NMR (500 MHz, DMSO-d6): delta(ppm) 25.700, 52.800, 104.161, 121.662, 146.010, 157.910, 159.124, 162.412, 162.949, 167.871.

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, 1161763-15-0, 4-Amino-6-bromo-2-methylpyrimidine.

Reference:
Patent; Nan Jing Cavendish Bio-Engineering Technology Co. Ltd.; Yan, Rong; Yang, Hao; Hou, Wen; Xu, Yongxiang; US2013/30177; (2013); A1;,
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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. 22536-65-8, name is 2-Chloro-5-methoxypyrimidine. A new synthetic method of this compound is introduced below., Computed Properties of C5H5ClN2O

Prepare 1L four-necked flask with a stirring device and thermometer.Add 100 g of 2-chloro-5-methoxypyrimidine,300 mL of acetic acid was added to the reaction flask,Stir well, then add 153g of 48% hydrobromic acid and 1g of methionine.Warming up to reflux reaction for 5 h,Sampling HPLC controlled until the end of the reaction, product content 96%, dihydroxy by-product 0.5%;After dropping to room temperature, 300 mL of water was added to the reaction solution, and the mixture was extracted three times with 300 mL of dichloromethane.The organic phases were combined and washed with saturated sodium bicarbonate solution.Then, it is dried over anhydrous sodium sulfate, and after filtration, the organic phase is concentrated under reduced pressure to give a crude product;The crude product was recrystallized from the crude product to give a pale yellow solid, 82 g.The yield was 91% and the purity was 98%.

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, 22536-65-8, 2-Chloro-5-methoxypyrimidine.

Reference:
Patent; Haimen Ruiyi Pharmaceutical Technology Co., Ltd.; Xue Song; Zhou Wenjun; (5 pag.)CN110041269; (2019); A;,
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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. 56843-79-9, name is 4-Chloro-2-methylthieno[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. name: 4-Chloro-2-methylthieno[2,3-d]pyrimidine

General procedure: Compounds 9-12 or 22-24 (1 equiv.) and corresponding chorides (1.2 equiv.) in AcOH/H2O:1/1 (20ml) were heated to 50C. When TLC analysis showed the complete conversion of the starting material, sodium hydroxide (2 equiv.) was added to the mixture. Then, the reaction mixture was extracted with ethyl acetate. After removal of the solvent, compounds 33-43 were purified by column chromatography and the corresponding compounds were obtained. Compounds 25-32 were used without further purification.

The synthetic route of 56843-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhi, Yanle; Li, Baoquan; Yao, Chao; Li, Hongmei; Chen, Puzhou; Bao, Jiyin; Qin, Tianren; Wang, Yue; Lu, Tao; Lu, Shuai; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 303 – 315;,
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Adding a certain compound to certain chemical reactions, such as: 22536-63-6, 2-Chloro-4-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, Quality Control of 2-Chloro-4-methoxypyrimidine, blongs to pyrimidines compound. Quality Control of 2-Chloro-4-methoxypyrimidine

Typical syntheses of these derivatives was performed by reaction of 2-broniopyridine, 2-chloiOpyrimidine, 4-amino-2-chloropyrimidine15, 2-chloro-4-methylpyrimidine165 2-chloro- 4-metlioxypyrimidine17 and 2-amino-4-chloropyrimidine1 with the corresponding 5-arnino-2- substitutedphenols in the presence of HCl, followed by reaction with 4-bromo-2~methyl-2- butene in presence of Cs2CO3 as a base. Compounds 46 and 47 were synthesized by reaction of 2-chloro-5-(pyrimidin-2-ylamino)phenol 35d with 4-methylpent-3-en-2-ol18 and (2- methylcyclopent-l-yl)methanol19, respectively, using Mitsunobu conditions20.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22536-63-6, 2-Chloro-4-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; YALE UNIVERSITY; WO2007/38387; (2007); A2;,
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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.83410-16-6, name is 4-Chloro-5-iodo-2,6-dimethylpyrimidine, molecular formula is C6H6ClIN2, molecular weight is 268.48, as common compound, the synthetic route is as follows.Computed Properties of C6H6ClIN2

Step 3 4-Chloro-2,6-dimethyl-5-(1-ethoxyvinyl)pyrimidine A mixture of 4-chloro-2,6-dimethyl-5-iodopyrimidine (13.5 g, 0.050 mol), (1ethoxyvinyl)tributyltin (20.0 g, 0.055 mol), lithium chloride (6.4 g, 0.150 mol), tetrakis(triphenylphosphine)palladium(0) (1.7 g, 0.0015 mol), and dioxane (100 mL) was heated under reflux for 23 h. Additional tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.0010 mol) was added and heating was continued for 25 h. The mixture was cooled, diluted with EtOAc, and! N KF (100 mL) was added. The solids were removed by filtration through Celite and the layers were separated. The organic phase was washed with pH 7 phosphate buffer (100 mL), brine (100 mL), dried MgSO4), and concentrated. Purification by flash chromatography (twice; 5-10% EtOAc/hexane) gave 6.44 g (61%) of product as a colorless oil. 1 H NMR (CDCl3) delta1.35 (t, J=7.0 Hz, 3H), 2.49 (s, 3H), 2.65 (s, 3H), 3.91 (q, J=7.0 Hz, 3H), 4.21 (d, J=2.8 Hz, 1H), 4.52 (d, J=2.8 Hz, 1H). Anal. calcd for C10 H13 ClN2 O: C, 56.47; H, 6.16; N, 13.17; Found: C, 55.13; H, 5.97; N, 13.16.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83410-16-6, 4-Chloro-5-iodo-2,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; American Home Products Corporation; US5466692; (1995); A;,
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Electric Literature of 1197953-49-3, 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 1197953-49-3, name is (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide. This compound has unique chemical properties. The synthetic route is as follows.

2-[D3]methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)aniline (1.25 g, 4.06 mmol), (2-((2,5-dichloropyrimidin-4-yl)amino)phenyl)dimethyl phosphine oxide (the compound of Formula IV) (0.92 g, 2.90 mmol), 14% hydrogenchloride-ethanol (7.5 g, 29 mmol) and ethylene glycol monomethyl ether (22mL) were respectively added in a 35 mLpressure tubing, heated in a microwave to 120C and reacted for 5.5 hours. After the reaction was completed, thereaction solution was cooled down to room temperature and evaporated under reduced pressure to remove the solvent.The residue was dissolved in dichloromethane (60mL) and adjusted to alkaline pH by adding saturated sodium carbonatesolution. The resulting solution was separated. The organic phase was washed with saturated brine (30 mL), dried overanhydrous sodium sulfate, and evaporated under reduced pressure to remove the solvent. The residue obtained wassubjected to silica gel column chromatography (mobile phase, dichloromethane : methanol : triethylamine = 300 : 30 :1.5) to give a crude product. The crude product was beaten with ethyl acetate (10 mL) to give (2-((5-chloro-2-((2-[D3]methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)amino)pyrimidin-4-yl)amino)phenyl)dimethyl phosphorusoxide (0.18 g, 11.0% yield), with >98% of D3 content.1H-NMR(300 MHz, CDCl3): delta = 10.80 (s, 1H), 8.62 (dd, J = 4.4, 8.2 Hz, 1H), 8.09-8.08 (m, 2H), 7.47 (dd, J = 7.7, 8.0Hz, 1H), 7.31-7.25 (m, 1H), 7.11 (dd, J = 7.4, 7.0 Hz, 1H), 6.54 (s, 1H), 6.48 (dd, J = 1.4, 8.4 Hz, 1H), 3.65 (d, J = 12.2Hz, 2H), 2.73-2.41 (m, 11H), 2.37 (s, 3H), 1.95 (d, J = 11.2 Hz, 2H), 1.85, 1.80 (2s, 6H), 1.73-1.66 (m, 2H).13C-NMR (75 MHz, CDCl3) : delta = 157.76, 155.87, 154.93, 149.29, 147.48, 143.90, 143.87, 132.33, 132.30, 129.52,129.37, 123.10, 123.01, 122.44, 122.27, 122.09, 120.58, 119.55, 108.36, 105.99, 101.01, 61.78, 55.27, 50.46, 48.78,45.83, 28.19, 19.02, 18.08.HRMS (ESI, [M+H]+) m/z: 587.2861.

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 1197953-49-3, (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide.

Reference:
Patent; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; ZHANG, Yinsheng; LIU, Baomin; YANG, Beibei; (35 pag.)EP3381925; (2018); A1;,
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