Pyrimidines

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. 4994-86-9, name is 4-Chloro-2-methylpyrimidine, molecular formula is C5H5ClN2, 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. name: 4-Chloro-2-methylpyrimidine

A solution of 4-chloro-2-methylpyrimidine (100 mg, 0.778 mmol), hexamethylditin (129 mu, 0.622 mmol), tetrakis(triphenylphosphine)palladium (0) (44.9 mg, 0.039 mmol) and 6-bromo-3-fluoro-2-(fluoromethyl)pyridine (113 mg, 0.544 mmol) in 1,4-dioxane was purged with nitrogen and irradiated in a microwave at 120 C for 1 h. The reaction mixture was allowed to cool to room temperature and diluted with ethyl acetate (25 mL). The black suspension was filtered through diatomaceous earth (Celite) and the bed was washed with ethyl acetate (10 mL). The filtrate was concentrated under reduced pressure. The black residue was purified via silica gel chromatography (0-25% petroleum ether in ethyl acetate) to afford 4-(5- fluoro-6-(fluoromethyl)pyridin-2-yl)-2-methylpyrimidine (35 mg, 0.123 mmol, 16% yield) as a brown semi-solid. LCMS (ESI) m/e 222.9 [(M+H)+, calcd for (S)-2-amino-2,4-dimethylpentan-1-ol

With the rapid development of chemical substances, we look forward to future research findings about 4994-86-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); A1;,
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Related Products of 2915-16-4 ,Some common heterocyclic compound, 2915-16-4, molecular formula is C16H11ClN2, 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.

Preparation of Compound 13 [115] Compound 1-10 (2.7 g, 10.11 mmol), Compound 1-9 (5 g, 10.11 mmol), Pd(PPh3)4 (584 mg, 0.50 mmol), K2CO3(2M) (15 mL) and EtOH (15 mL) were dissolved in toluen (30 mL), and the mixture was heated at 120 . After the mixture was stirred for 3 hours, the reaction was completed. The reaction mixture was washed with distilled water and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 13 (5 g, 72%) was obtained through purification by column chromatography.

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. 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; KIM, Hye Mi; KIM, Young Gil; CHO, Young Jun; KWON, Hyuck Joo; KIM, Bong Ok; KIM, Sung Min; WO2011/93609; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 63558-65-6, 4-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, Quality Control of 4-Chloro-5-iodopyrimidine, blongs to pyrimidines compound. Quality Control of 4-Chloro-5-iodopyrimidine

Under nitrogen, a mixture of 4-chloro-5-iodopyrimidine (2.0 g, 8.32 mmol), 2- (methylthio)-4-(tributylstannyl)pyrimidine (3.8 g, 9.15 mmol) and bis(triphenylphosphine)palladium(II) chloride (1.12 g, 1.60 mmol) in toluene (70 mL) was stirred for 16 h at 95 C. The reaction was quenched with a saturated solution of potassium fluoride. The mixture was extracted with ethyl acetate and washed with brine. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica flash chromatography (ethyl acetate/petroleum ether 20:80) to afford the title compound (534 mg, 26.9% yield) as a yellow solid. LCMS (ESI): [M+H]+ = 239.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63558-65-6, 4-Chloro-5-iodopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; BRAUN, Marie-Gabrielle; GIBBONS, Paul; LEE, Wendy; LY, Cuong Q.; RUDOLPH, Joachim; SCHWARZ, Jacob Bradley; ASHKENAZI, Avi; BEVERIDGE, Ramsay; ZHAO, Liang; LEMIRE, Alexandre; FU, Leo; LAI, Kwong Wah; WANG, Fei; (100 pag.)WO2020/56061; (2020); A1;,
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Reference of 672-41-3, 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. 672-41-3, name is 6-(Trifluoromethyl)pyrimidin-4-amine, molecular formula is C5H4F3N3, 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 6-(trifluoromethyl)pyrimidin-4-amine (0.14544 g, 0.89175 mmol) and 2-bromo-1-(5- bromo-3-ethylsulfonyl-2-pyridyl)ethanone (0.3 g, 0.81 mmol) in acetonitrile (9mL) were heated for 1 h at 150C in the microwave. After this time, the reaction mixture was evaporated. The solid obtained was dissolved in dichloromethane and washed with NaHC03 sat sol. The organic layer was then washed with brine, dried over Na2S04, filtered and concentrated in vacuo. Purification by Combi flash chromatography with a column of 12 g and a gradient of dichloromethane + 0-10% ethylacetate gave the title product as white powder. LCMS (method 1 ); Rt= 0.91 min, [M+H] 435/437. H NMR (400 MHz, chloroform-c/) delta ppm: 1 .40 (t, J=7.52 Hz, 3 H); 4.00 (q, J=7.46 Hz, 2 H); 7.97 (s, 1 H); 8.36 (s, 1 H); 8.69 (d, J=2.20 Hz, 1 H); 8.95 (d, J=2.20 Hz, 1 H); 9.17 (s, 1 H).

According to the analysis of related databases, 672-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; EDMUNDS, Andrew; JEANGUENAT, Andre; JUNG, Pierre Joseph Marcel; MUEHLEBACH, Michel; (150 pag.)WO2016/71214; (2016); A1;,
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Pyrimidine – Wikipedia

Related Products of 1005-37-4, Adding some certain compound to certain chemical reactions, such as: 1005-37-4, name is 6-Chloro-N4-methylpyrimidine-2,4-diamine,molecular formula is C5H7ClN4, 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 1005-37-4.

Intermediate 41 -(3-aminophenyl)-4-N-methylpyrimidine-2,4-diamine. Tetrakis(triphenylphosphine)palladium (0) (5 mol%) was added to a stirred mixture of 6-chloro-4-N-methylpyrimidine-2,4-diamine (1.00 mmol), (3- aminophenyl)boronic acid (1.3 equiv.), sodium carbonate (3.2 equiv.), 1 ,4- dioxane (4 mL) and water (1 mL) in a tube. The tube was sealed and the reaction was heated at 90C for 5 h and then concentrated. The crude material was taken up in ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate, concentrated and purified by flash chromatography (0?15 % MeOH in DCM) to give the title compound. LCMS [M+H]+ 216.

According to the analysis of related databases, 1005-37-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); 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.59549-51-8, name is 5-Bromo-2-chloro-4-(methylthio)pyrimidine, molecular formula is C5H4BrClN2S, molecular weight is 239.52, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-2-chloro-4-(methylthio)pyrimidine

A 3-L, 3-neck, round-bottom flask was equipped with a J-KEMtemperature controller, a mechanical stirrer, and a nitrogen inlet. The flask was charged with 5-bromo-2-chloro-4-(methylthio)pyrimidine (100 g, 417.5 mmol), (lr,4r)-4- aminocyclohexanol (76.4 g, 663.4 mmol), and ethanol (1 L). DIEA (109 mL,626.3 mmol) was added, and the mixture was heated to reflux overnight. TLC (1 : 1 hexanes/ethyl acetate) analysis after 20 h indicated complete reaction. The reaction was allowed to cool to room temperature. Water (300 mL) was added, and a precipitate gradually formed. The solid was filtered and washed with water to give 111.7 g of a white solid. The filtrate was extracted with ethyl acetate (3 x 300 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to a semi-solid. The semi-solid was slurried in 1 : 1 hexanes/ethyl acetate and filtered to give an additional 12.1 g of a white solid. The two batches were combined to give 123.8 g (93%) of (lr,4r)- 4-(5-bromo-4-(methylthio)pyrimidin-2-ylamino)cyclohexanol as a white solid. MS (ESI) m/z 318, 320 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59549-51-8, 5-Bromo-2-chloro-4-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
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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. 335654-06-3, name is 2-Chloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., category: pyrimidines

4-methoxy-7H-pyrrolo[2,3-d]pyrimidine (3) or 2-methoxy-7H-pyrrolo[2,3-d]pyrimidine (4) is prepared by reacting 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1) or 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (2), respectively, with sodium hydroxide in methanol as described by Girgis, N. et.al., J. Heterocyclic. Chem. 1989, 26:317-325.

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, 335654-06-3, 2-Chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Plexxikon, Inc.; US2009/286783; (2009); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 84905-80-6, 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.84905-80-6, name is 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

Example 171 Production of N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5-[2-(2-methoxyethoxy)ethyl]-5H-pyrrolo[3,2-d]pyrimidin-4-amine hydrochloride 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (500 mg) was dissolved in N,N-dimethylformamide (10 mL), and potassium carbonate (830 mg) and 2-(2-methoxyethoxy)ethyl 4-methylbenzenesulfonate (920 mg) were added and the mixture was stirred at room temperature for 12 hrs. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=50:50 ? 0:100). The obtained oil was dissolved in isopropyl alcohol (10 mL), and 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline was added. The mixture was stirred at 90C for 4 hrs, saturated aqueous sodium hydrogen carbonate was added to the reaction mixture under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated. The residue was separated and purified by silica gel column chromatography (eluent, ethyl acetate_methanol=100:0 ? ethyl acetate_methanol=90:10), and crystallized from 4N hydrochloric acid-ethyl acetate solution/hexane to give the title compound (277 mg). 1H-NMR(DMSO-d6) delta: 3.06 (3H, s), 3.33 – 3.35 (2H, m), 3.55 – 3.61 (2H, m), 3.83 – 3.86 (2H, m), 4.83 – 4.86 (2H, m), 6.71 (1H, d, J= 3 Hz), 7.24 – 7.72 (7H, m), 7.99 – 8.04 (2H, m), 8.77 (1H, s), 9.92 (1H, s).

Statistics shows that 84905-80-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1752457; (2007); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 659729-09-6, 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 659729-09-6, name is 4-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

1.27 g (4.92 mmol) of 4-chloro_6_ (4′-trifluoromethylphenyl) pyrimidine was weighed out,(0.85 g, 5.18 mmol) of trimethylbenzeneboronic acid,4 g of tetrakis (triphenylphosphine) palladium and 3 g of anhydrous sodium carbonate were placed in a 120 mL sealed tube,A mixture of tetrahydrofen sitan 30 mL and 20 mL of deionized water was placed in a sealed tube as a solvent, and a stirrer was added and the stopper was capped.The entire device vacuum nitrogen nitrogen replacement 3 ~ 4 times, placed in the oil bath pot,The mixture was heated to 115 C on a magnetic stirrer and refluxed for about 8 h.After the reaction,Sealed to cool to room temperature, the solution inside the sealed tube into the rotary bottle,The tetrahydrofuran solvent was distilled off under reduced pressure by rotary evaporator.The organic product was extracted with ethyl acetate and water for 3 to 4 times. The solvent was distilled off under reduced pressure. The spheroidized product was separated by petroleum ether: ethyl acetate 20: 1,To give a pale yellow solid, about 0.87 g, yield 51.6%.

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 659729-09-6, 4-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine.

Reference:
Patent; Anhui University of Technology; Tong Bihai; He Yuheng; Liu Yuanyuan; Jin Long; Zuo Dashuai; Wang Song; (25 pag.)CN106632488; (2017); 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. 955368-90-8, name is 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one

Compound 1.1 (255 mg, 1 mmol),2-allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (222 mg, 1 mmol),Cuprous iodide (191 mg, 1 mmol),Anhydrous potassium carbonate (276 mg, 2 mmol)And N,N-dimethylethylenediamine (88 mg, 1 mmol)Add to 1,4-dioxane (20 mL),The reaction system was stirred at 100 C overnight.The reaction solution was then cooled to room temperature.filter,The filtrate is concentrated,The residue was purified by silica gel column chromatography (EtOAc /EtOAcCompound 1-1 (205 mg, yield: 52%) was a red liquid.

The synthetic route of 955368-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Dinuo Pharmaceutical Technology Co., Ltd.; Zhao Zhiming; Gao Daxin; Chen Shoujun; Wu Zhiheng; (105 pag.)CN108623615; (2018); A;,
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