Pyrimidines

Application of 131860-97-4, 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.131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, molecular formula is C15H13ClN2O4, molecular weight is 320.73, as common compound, the synthetic route is as follows.

A slurry containing methyl (E)-I- {2-[6~chloropyrimidin-4-yloxy]phenyl} -3-methoxyacrylate (80.9g at 99%, 0.25mols), potassium carbonate (52.8g at 98%, 0.375mols) and 2- cyanophenol (33.6g at 97.5%, 0.275mols) in MIBK (16OmIs) was heated to approximately 6O0C. A solution of DABCO (0.28g, 0.0025mols) in MlBK (1 OmIs) was added. The mixture was heated to 8O0C and held at this temperature for 360 minutes. Water (30OmIs) was charged to the reaction, maintaining the temperature in the range 70-800C. The mixture was stirred for 70 minutes then settled and the lower aqueous phase separated. The MIBK solution (235.3g) contained methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4- yloxyjphenyl} -3-methoxyacrylate (41.0%w/w) 95.8% of theory.; c) Coupling of methyl rE)-2-{2-[6-chloropyrimidin-4-yloxylphenyl|-3-methoxyacrylate with 2-cvanophenol in MIBK with lmol% DABCO added after the 2-cyanophenol, that is, last. EPO A slurry containing methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (80.9g at 99%, 0.25mols), potassium carbonate (52.8g at 98%, 0.375mols) and 2- cyanophenol (33.6g at 97.5%, 0.275mols) in MIBK (16OmIs) was heated to approximately 6O0C. A solution of DABCO (0.28g, 0.0025mols) in MBK (1 OmIs) was added. The mixture was heated to 8O0C and held at this temperature for 240 minutes (residual (¡ê)-2- {2-[6- chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate at the end of reaction was 4.4% by area on GC). Water (30OmIs), at 6O0C, was charged to the reaction, maintaining the temperature in the range 70-800C. The mixture was stirred for 40 minutes then settled and the lower aqueous phase separated. The MIBK solution (237.Ig) contained methyl (E)-2-{2-[6-(2- ” cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (38.7%w/w) 89.1% of theory.

Statistics shows that 131860-97-4 is playing an increasingly important role. we look forward to future research findings about (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate.

Reference:
Patent; SYNGENTA LIMITED; WO2006/114572; (2006); A2;,
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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. 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, molecular formula is C17H13N5O, 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. HPLC of Formula: C17H13N5O

a) 4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]benzaldehyde 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.0 g, 6.59 mmol) was mixed with 4-fluorobenzaldehyde (1.06 mL, 9.89 mmol), cesium carbonate (4.30 g, 13.19 mmol) in DMF (6 mL). The reaction mixture was heated at 86 C. overnight. After cooling to room temperature, the reaction mixture was poured onto ice water. The solid was collected by filtration to give 4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]benzaldehyde (2.46 g, 92%). 1H NMR (CDCl3) delta 7.19 (m, 5H), 7.46 (m, 2H), 7.78 (d, J=8.64 Hz, 2H), 8.10 (d, J=8.70 Hz, 2H), 8.44 (s, 1H), 8.59 (d, J=8.70 Hz, 2H), 10.03 (s, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 330786-24-8.

Reference:
Patent; Abbott Laboratories; US6921763; (2005); B2;,
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Adding a certain compound to certain chemical reactions, such as: 153435-63-3, 2-(Tributylstannyl)pyrimidine, 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, 153435-63-3, blongs to pyrimidines compound. Quality Control of 2-(Tributylstannyl)pyrimidine

Intermediate 3 (75mg;1 eq) was dissolved in dry DMF (2ml), then CsF (49mg;2 eq), Cul (6mg;0.2 eq), [Ph3P]4Pd (19mg; 0.1 eq) and 2- pyrimidyltributylstannane(90mg;1 .5 eq; prepared according to Eur. J. Org. Chem. 2003, 171 1 -1721 ) were added. The mixture was warmed at 130C for 25 minutes (microwave), then poured in aqueous saturated solution of NH4CI and extracted with DCM. The organic layers were combined, washed with water, dried (Na2SO4) and concentrated under vacuum; crude product was purified by silica gel column chromatography (Cyclohexane/AcOEt 9/1 to AcOEt) then by SCX cartridge (5g) to obtain 13mg of the title compound.MS (ESI) m/z 468-470 ;1 HNMR (CDCI3) delta ppm 8.80-8.94 (m, 1 H), 8.66 (d, 1 H), 8.22-8.43(m, 1 H), 7.86- 8.07 (m, 1 H), 7.12-7.52(m, 4H), 6.22-6.74(m, 1 H), 4.98-5.22(m, 1 H),4.32-4.81 (m, 1 H), 3.08-3.97(m, 4H), 1 .90-2.40(m, 2H), 0.65-1 .65 (m, 2H), 0.15-0.65 (m, 4H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153435-63-3, its application will become more common.

Reference:
Patent; ROTTAPHARM S.P.A.; STASI, Luigi Piero; ROVATI, Lucio; WO2012/104338; (2012); A1;,
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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. 89793-12-4, name is Ethyl 2-chloropyrimidine-5-carboxylate, the common compound, a new synthetic route is introduced below. category: pyrimidines

To a solution of compound 4 (2.29 g 10 mmol) in dioxane (50 ml) was added compound 5 (1.87 g, 1.0 equiv.) and DIPEA (2.58 g, 2.0 equiv.). The mixture was heated overnight at 110-120 ¡ãC. The resulting mixture was directly purified on silica gel column to afford the coupled product, compound 6, as a white solid (1.37 g, 40percent)

The synthetic route of 89793-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACETYLON PHARMACEUTICALS, INC.; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; JONES, Simon, S.; QUAYLE, Steven, N.; SAHAKIAN, Eva; IBARZ, Javier, Pinilla; (83 pag.)WO2017/184774; (2017); A1;,
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Synthetic Route of 7226-23-5 ,Some common heterocyclic compound, 7226-23-5, molecular formula is C6H12N2O, 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 solution of diisopropylamine (3.4 mL, 24.38 mmol) in dry tetrahydrofuran (21 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7 mL) was cooled to -78 C. under nitrogen and then treated with a 2.5M solution of n-butyllithium in hexanes (9.8 mL, 24.38 mmol). The resulting reaction mixture was stirred at -78 C. for 30 min and then treated dropwise with a solution of (3-bromo-4-methylsulfanyl-phenyl)-acetic acid methyl ester (6.10 g, 22.17 mmol) in dry tetrahydrofuran (21 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7 mL). The resulting reaction mixture was allowed to stir at -78 C. for 1 h, at which time, a solution of iodomethylcyclopentane (5.59 g, 26.60 mmol) in a small amount of dry tetrahydrofuran was added dropwise. The reaction mixture was allowed to warm to 25 C. where it was stirred for 15 h. The reaction mixture was quenched with water (300 mL) and then concentrated in vacuo to remove tetrahydrofuran. The remaining aqueous phase was extracted with ethyl acetate (3*150 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1*200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 19/1 hexanes/ethyl acetate) afforded 2-(3-bromo-4-methylsulfanyl-phenyl)-3-cyclopentyl-propionic acid methyl ester (4.52 g, 57%) as a light yellow oil: EI-HRMS m/e calcd for C16H21BrO2S (M+) 356.0446, found 356.0435.

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. 7226-23-5, 1,3-Dimethyltetrahydropyrimidin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bizzarro, Fred Thomas; Corbett, Wendy Lea; Grippo, Joseph Francis; Haynes, Nancy-Ellen; Holland, George William; Kester, Robert Francis; Sarabu, Ramakanth; US2001/39344; (2001); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7752-78-5, 5-Bromo-2-methylpyrimidine, 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, 7752-78-5, blongs to pyrimidines compound. SDS of cas: 7752-78-5

A stirred solution of 5-bromo-2-methylpyrimidine(A18, 0.5 g 2.8 mmol), ethyl 6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)imidazo[l,2-a]pyridine-2- carboxylate(1-26, 1.55 g, 4.9 mmol) and sodium carbonate(0.612 g, 5.7 mmol) in dioxane : water(4:1) 15 mL was degassed with argon for 20 minutes. Then[I,G- Bis(diphenylphosphino)ferrocene]palladium(II) dichloride(0.126 g, 0.17 mmol) was added. The reaction mixture was heated at 90C for 16 h. After completion, reaction mixture quenched with water and extracted with 20% MeOH in DCM(3 times). The organic layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude. This crude purified by combiflash using 3% MeOH in DCM as eluent. The desired fractions were concentrated under reduced pressure to offered ethyl 6-(2-methylpyrimidin-5-yl)imidazo[l,2-a]pyridine-2-carboxylate 1-28 as dark solid. Yield: 0.64 g(78%) LC-MS(ES) m/z = 283.3[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,7752-78-5, its application will become more common.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VADIVELU, Saravanan; RAJAGOPAL, Sridharan; BURRI, Raghunadha Reddy; GARAPATY, Shivani; SIVANANDHAN, Dhanalakshmi; THAKUR, Manish Kumar; NATARAJAN, Tamizharasan; SWAMY, Indu N; NAGARAJU, Nagendra; KANAGARAJ, Subramaniam; MOHD, Zainuddin; SARKAR, Sayantani; SAMANTA, Swapan Kumar; ., Hariprakash; (284 pag.)WO2019/102494; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

Load 0.105 mol 2-cyanophenol, 0.11 mol anhydrous potassium carbonate, and 100 ml butyl acetate into a 500 ml glass line reactor kettle, heat up to 70 C. while stirring, add 0.1 mol (E)-2-[2-(6-chloropyrimidine-4-methoxy)-phenyl]-3-methoxy methyl acrylate (the compound represented by formula (2), from J&K Chemical Limited, at 95% purity) and a catalyst (0.004 mol 2-methyl-1,4-diazabicyclo[2.2.2]-octane (from Qingdao Hanbing Chemical Co., Ltd., at 99% purity)), continue to heat up the reaction mixture to 105 C. and hold at the temperate for 4 h to perform reaction, and monitor the reaction situation with a gas chromatograph, add 50 ml into the reaction system when the gas chromatograph indicates that the normalized area of (E)-2-[2-(6-chloropyrimidine-4-methoxy)-phenyl]-3-methoxy methyl acrylate is smaller than 1%, after stirring for 60min., and then stand for 10 min. at 80 C. for stratification, remove the aqueous phase, and add water to wash the organic phase again, cool down the obtained organic phase to -5 C. to precipitate crystals, then, filter to obtain 51.3 g wet filter cake, rinse the filter cake with butyl acetate, heat up the rinsed filter cake to approx. 50-60 C. with 100 ml methanol to pulping and wash, and then filter and dry; finally, 37 g yellowish white solid is obtained, and the melting point of the solid is 115-116 C. Test 10 mg solid product by NMR. The data is 1H NMR(500NMR, CDCl3): delta 3.64(s, 3H), 3.75(s, 3H), 3.62(s, 2H), 6.42(d, 1H), 7.22(q,1H), 7.29-7.43(m, 5H), 7.49(s, 1H), 7.66(m, 1H), 7.10(q, 1H), 8.40(d, 1H), which fully matches the theoretical value of the compound represented by formula (1), indicating that the product is the compound represented by formula (1). The calculated yield ratio of the product is 95.0%, and the purity is 99.5%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, and friends who are interested can also refer to it.

Reference:
Patent; NUTRICHEM COMPANY LIMITED; SHANGYU NUTRICHEM CO., LTD.; Wang, Wenjun; Chen, Jianwei; Chi, Jianhong; Zhao, Yongchang; Deng, Xufang; Wang, Long; You, Hua’nan; (9 pag.)US2016/90365; (2016); A1;,
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Electric Literature of 62208-68-8, 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 62208-68-8 as follows.

Intermediate I-3 (20 g, 98.9 mmol)Dissolve in a 500 mL round bottom flask with 300 mL of phosphorus oxychloride.Cool down to -30 C,N,N-Diisopropylethylamine (25.6 g, 0.2 mol) was added slowly.The mixture was stirred under reflux for 36 hours, and then cooled to room temperature.The reaction solution was poured into ice water and extracted with ethyl acetate.The extracted organic phase is washed with a saturated sodium hydrogen carbonate solution.And remove water with sodium sulfate.The treated organic phase was concentrated to dryness to give Intermediate I-4 (10.6 g, 45%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62208-68-8, its application will become more common.

Reference:
Patent; Zhejiang Huaxian Optoelectric Technology Co., Ltd.; Zheng Xianzhe; Huang Dong; Hua Wanming; Quan Meizi; Zhao Xiaoyu; (34 pag.)CN109678868; (2019); A;,
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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. 591-55-9, name is 5-Aminopyrimidine. A new synthetic method of this compound is introduced below., COA of Formula: C4H5N3

To a degassed DMF (12 mL) in a sealed reactor were added tert-butyl 2-(3-acetyl-5-bromo- lH-indol-l-yl)acetate (90b) (1.05 g, 2.98 mmol), cesium carbonate (1.94 g, 5.96 mmol), pyrimidin-5-amine (340 mg, 3.58 mmol), Pd2(dba)3 (273 mg, 0.3 mmol), (9,9-dimethyl-9H- xanthene-4,5-diyl)bis(diphenylphosphine) (Xanthphos, 172 mg, 0.3 mmol) and heated with stirring at 100 C for 16 h. The mixture was cooled to room temperature, diluted with EtOAc (30 mL) and filtered over Celite pad. The pad was washed with EtOAc (2 x 15 mL) and combined filtrate was concentrated to give a crude residue which was purified by flash column chromatography [silica gel (40 g), eluting with CMA80 in CHCb 0 to 20%] to afford tert-butyl 2-(3-acetyl-5-(pyrimidin-5-ylamino)-lH-indol-l-yl)acetate (97a) (0.34 g, 0.93 mmol, 31% yield) as light yellow solid; MS (ES+): 367.5 (M+l), MS (ES-): 401.4 (M+Cl).

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, 591-55-9, 5-Aminopyrimidine.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; ZHANG, Weihe; VOGETI, Lakshminarayana; WU, Minwan; CHINTAREDDY, Venkat, R.; RAMAN, Krishnan; (479 pag.)WO2017/136395; (2017); A1;,
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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 6630-30-4, name is 6-Chloro-5-nitropyrimidine-2,4-diol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-Chloro-5-nitropyrimidine-2,4-diol

6-Chloro-5-nitro-1H-pyrimidine-2,4-dione (25.6 g, 134 mmol) is mixed with THF (300 mL) and cooled to 0 C. Sodium thiomethylate (25.0 g, 357 mmol) is added in portions (temperature<5 C.). The reaction mixture is stirred for 16 h, poured into hydrochloric acid (1 M in H2O; 1000 mL) at 0 C. and stirred for 1 h. The precipitate is filtered off, washed with ice-water and EA and dried to yield the product that is taken to the next step without further purification. [0420] Rf (EA/MeOH 8:2)=0.28 With the rapid development of chemical substances, we look forward to future research findings about 6630-30-4. Reference:
Patent; Boehringer Ingelheim International GmbH; GERLACH, Kai; EICKMEIER, Christian; HEINE, Claudia; HEINE, Niklas; WEBER, Alexander; US2013/225549; (2013); A1;,
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