Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 183438-24-6, 5-Bromo-2-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, Formula: C4H2BrIN2, blongs to pyrimidines compound. Formula: C4H2BrIN2

Step 1: 5-Bromo-2-phenyl-pyrimidine To a degassed solution of phenylboronic acid (8.93 g, 73.22 mmol, 1.0 equiv; commercially available), 5-bromo-2-iodo-pyrimidine (20.86 g, 73.22 mmol, 1.0 equiv; commercially available) and tetrakis(triphenylphosphine) palladium(0) (0.85 g, 0.73 mmol, 0.01 equiv) in toluene (180 mL) was added Na2CO3 (15.52 g, 146.45 mmol, 2.0 equiv), dissolved in water (60 mL), and the reaction mixture heated to reflux. After 18 h, tetrakis(triphenylphosphine) palladium(0) (0.42 g, 0.37 mmol, 0.005 equiv) was added and the reaction mixture heated for an additional time period of 24 h. The solvent was removed under reduced pressure and the crude reaction product extracted from a sat. solution of NaCl (200 mL) with ethyl acetate (3*150 mL). The combined organic phases were dried over Na2SO4, concentrated by evaporation under reduced pressure and the crude material purified by silica column chromatography eluding with heptane/ethyl acetate (9:1) to provide 8.60 g (50percent) of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,183438-24-6, 5-Bromo-2-iodopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Christ, Andreas D.; Martin, Rainer E.; Mohr, Peter; US2008/64697; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 14080-23-0, 2-Cyanopyrimidine, 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, name: 2-Cyanopyrimidine, blongs to pyrimidines compound. name: 2-Cyanopyrimidine

(i) Synthesis of pyridine-2-carboxyamidrazone A synthesis scheme of pyridine-2-carboxyamidrazone is shown in (E-1). In a 50 mL recovery flask were placed 3.2 g (3.0 mmol) of 2-cyanopyridine, 15 mL of ethanol, 5.0 mL of water, and 2.0 mL (41 mmol) of hydrazine monohydrate. This solution was stirred at room temperature for 26 hours under a nitrogen stream. After a certain time, a saturated saline was added to the solution. This solution was extracted with chloroform, and the extract was dried with magnesium sulfate. The mixture was subjected to gravity filtration, and the obtained filtrate was concentrated to give 1.7 g of a target substance, yellow oily substance in a yield of 40%.

The synthetic route of 14080-23-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; US2012/178933; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 49844-90-8, 4-Chloro-2-(methylthio)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, 49844-90-8, blongs to pyrimidines compound. Formula: C5H5ClN2S

A mixture of 4-chloro-2-(methylsulfanyl)pyrimidine (2 g, 12.45 mmol), (2,6- difluoro-4-pyridyl)boronic acid (3.95 g, 24.90 mmol) , Cs2C03 (8.11 g, 24.90 mmol) and (dppf)PdCl2-DCM (1.07 g, 1.24 mmol) in water (15 mL) and MeCN (45 mL) was degassed with N2, capped in a glass reaction tube (150 mL), heated at 95 C for 2.5 h. After cooled, it was filtered through a short pad of CELITE, diluted with water, extracted with EtOAc (2 x 80 mL), dried (Na2S04), filtered and concentrated on CELITE. The crude product was purified by Si02 chromatography (ISCO 40 g column) and eluded with an EtOAc/heptane gradient (0 to 15% EtOAc) to afford 2.66 g (89%) of 4-(2,6-difluoropyridin-4-yl)-2- (methylthio)pyrimidine as white solid. MS: m/z 239.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,49844-90-8, its application will become more common.

Reference:
Patent; GENENTECH, INC.; KOLESNIKOV, Aleksandr; DO, Steven; WO2015/85007; (2015); A1;,
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Electric Literature of 1421372-94-2, 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 1421372-94-2 as follows.

To a solution of 1 (393 mg, 1 mmol) and thiomorpholine(154 mg, 1.5 mmol) in DMF (20 mL), DIPEA (194 mg, 1.5 mmol) wasadded. After stirring at 60 C for 4 h, the mixture was poured intoice water. The resulting precipitate was filtered off, washed withwater, and dried under vacuum to give the product as a yellowsolid. 66% yield. 1H NMR (400 MHz, Chloroform-d) d 9.62 (s, 1H),8.39 (t, J 5.1 Hz, 1H), 8.25 (s, 1H), 8.17 (dd, J 6.4, 2.5 Hz, 1H), 7.59(s, 1H), 7.45e7.39 (m, 1H), 7.31 (td, J 4.2, 3.6, 1.9 Hz, 1H), 7.20 (dd,J 8.2, 5.3 Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H), 3.94 (s, 3H), 3.39e3.25(m, 4H), 2.90e2.77 (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,1421372-94-2, its application will become more common.

Reference:
Article; An, Baijiao; Pan, Tingting; Hu, Jinhui; Pang, Yanqing; Huang, Ling; Chan, Albert S.C.; Li, Xingshu; Yan, Jun; European Journal of Medicinal Chemistry; vol. 183; (2019);,
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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. 160199-05-3, name is 2,4-Dichlorobenzo[4,5]thieno[3,2-d]pyrimidine, the common compound, a new synthetic route is introduced below. Product Details of 160199-05-3

2000 mL round bottom flask 25.0 g intermediate A ( 98.5 mmol ) , phenyl-3 – Boro Nick ester – carbazole 40.01 g (108.35 mmol, dealer : Beijing Green Technology Guardee) , potassium carbonate 34.04 g (246.26 mmol), Pd ( PPh3) 4(Tetrakis (triphenylphosphine)? Palladium (0)) 5.7 g (4.93 mmol) and 1,4- dioxane 600 mL , placed in 300 mL waterGave was then heated to reflux for 6 hours in a nitrogen stream . Inflicting a mixture obtained therefrom in 1500 mL of methanolAfter filtration over a solid crystallized , it was dissolved in monochlorobenzene , and filtered through a silica gel / Celite , an appropriate amount of an organic solventAfter removal , by re-crystallization with methanol to give the intermediate 16 – A ( 31.85 g , yield 70% ) .

The synthetic route of 160199-05-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI co . Ltd; Samsung Electronics Co., Ltd.; Kim, Byeong Gu; Jong, Ho Gook; Han, Soo Jin; Kwon, Oh Hyeon; Kim, Young-Gwon; Kim, Chang Woo; Kim, Heong Son; Seo, Ju Hui; Shin, Chang Joo; Yu, Eun Son; Lee, Seung-Jae; Choe, Byeong Gi; Hwang, Gyu Young; (229 pag.)KR2015/84657; (2015); A;,
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Application of 1979-96-0, 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. 1979-96-0, name is 4,6-Dichloro-2-(methylthio)-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

Compound BTo a solution of compound A (2.46 g, 10.2 mmol) in THF (34 mL) at -20 C. was added Et3N (3.14 mL, 22.5 mmol) followed by a solution of NH3 (2.0 M in MeOH, 5.4 mL, 11 mmol). The mixture was stirred while warming to 0 C. for 1.5 h (LC/MS indicated consumption of starting materials). The reaction mixture was taken forward without work-up.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1979-96-0, 4,6-Dichloro-2-(methylthio)-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Gilead Sciences, Inc.; US2010/143301; (2010); 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. 6299-25-8, name is 4,6-Dichloro-2-(methylthio)pyrimidine, the common compound, a new synthetic route is introduced below. Computed Properties of C5H4Cl2N2S

Reference Example 71 Production of ethyl 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carboxylate Under an argon atmosphere, to a solution of diisopropylamine (15.7 mL, 112 mmol) in THF (70 mL) was added dropwise butyllithium (1.6M hexane solution, 70 mL, 112 mmol) at -78C. The mixture was stirred at 0C for 30 min and cooled to -78C. A solution of 4,6-dichloro-2-(methylsulfanyl)pyrimidine (14.12 g, 72.4 mmol) in THF (20 mL) was added dropwise thereto, and the mixture was stirred at – 78C for 1 hr. A solution of ethyl chlorocarbonate (13.9 mL, 145 mmol) in THF (20 mL) was added dropwise thereto, and the mixture was stirred at -78C for 30 min, and then at 0C for 30 min. Water was added thereto, and the mixture was extracted twice with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=100:0?90:10) to give the title compound (13.28 g, 69%) as a colorless solid.

The synthetic route of 6299-25-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2471793; (2012); A1;,
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Electric Literature of 2227-98-7, 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.2227-98-7, name is 4-Aminopyrrolo[3,2-d]pyrimidine, molecular formula is C6H6N4, molecular weight is 134.14, as common compound, the synthetic route is as follows.

9- Deazaadenine (73 mg, 0.55 mmol), (¡À)-66 (80 mg, 0.37 mmol) and aq. formaldehyde (37%,044 mL, 0.55 mmol) were stirred for 1 h in a mixture of 1,4-dioxane (2 mL) and H2O (0.5 mL) at 90 oC (bath temp). The reaction mixture was cooled to rt and NH3 in MeOH solution (7 M, 2.5 mL) was added and the resulting reaction left to stir for a further 1 h. The solventwas evaporated and the residue chromatographed (CH2Cl2-7 M NH3 in MeOH, 9:1 thenCH2Cl2-7 M NH3 in MeOH, 8:2) to afford (¡À)-67 as a syrup (110 mg) which by 1H NMR was contaminated with paraformaldehyde. A portion of crude (¡À)-67 (65 mg) was dissolved inS24MeOH (5 mL) and aq. HCl (37%, 0.5 mL) added. The solvent was evaporated and the residue dissolved in more aq. HCl (37%, 0.5 mL) then the solvent evaporated again. The residue was chromatographed (CH2Cl2-7 M NH3 in MeOH, 85:15 then CH2Cl2-7 M NH3 inMeOH, 8:2) to give (¡À)-68 as a syrup (35 mg, 61%).

Statistics shows that 2227-98-7 is playing an increasingly important role. we look forward to future research findings about 4-Aminopyrrolo[3,2-d]pyrimidine.

Reference:
Article; Clinch, Keith; Evans, Gary B.; Froehlich, Richard F.G.; Gulab, Shivali A.; Gutierrez, Jemy A.; Mason, Jennifer M.; Schramm, Vern L.; Tyler, Peter C.; Woolhouse, Anthony D.; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5181 – 5187;,
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Reference of 1209459-16-4 ,Some common heterocyclic compound, 1209459-16-4, molecular formula is C5H2BrN3, 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.

Example 11 Preparation of (3S)-tert-butyl 3-((1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)(3,5-difluorophenyl)carbamoyl)-4-(4-cyanopyrimidin-2-yl)-5-oxopiperazine-1-carboxylate (racemic)-Compound 98 A mixture of (3S)-tert-butyl3-((1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)(3,5-difluorophenyl)carbamoyl)-5-oxopiperazine-1-carboxylate (200 mg, 0.326 mmol), 2-bromopyrimidine-4-carbonitrile (0.489 mmol), Pd2(dba)3 (30.2 mg, 0.0323 mmol), XantPhos (19.1 mg, 0.03 mmol) and Cs2CO3 (148.7 mg, 0.46 mmol) in 1,4-dioxane (10 mL) was stirred at 80 C. for 3 hr under N2. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated and the residue was purified by a standard method to afford the desired product. 1H NMR (400 MHz, CDCl3): delta 8.97 (d, J=4.3 Hz, 1H), 7.85-7.55 (d, 1H), 7.51-7.39 (m, 2H), 7.25 (t, J=7.6 Hz, 1H), 7.13-6.26 (m, 6H), 5.91 (d, J=7.6 Hz, 1H), 4.92-4.08 (m, 5H), 3.38 (t, J=14.9 Hz, 1H), 3.02 (s, 2H), 2.83-2.22 (d, 2H), 1.61 (s, 9H). MS: 716.1 (M+1)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1209459-16-4, its application will become more common.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC; Lemieux, Rene M.; Popovici-Muller, Janeta; Travins, Jeremy; Cai, Zhenwei; Cui, Dawei; Zhou, Ding; US2013/190249; (2013); A1;; ; Patent; AGIOS PHARMACEUTICALS, INC; Lemieux, Rene M.; Popovici-Muller, Janeta; Travins, Jeremy; Cai, Zhenwei; Cui, Dawei; Zhou, Ding; US2015/31627; (2015); A1;,
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Synthetic Route of 111196-81-7 , The common heterocyclic compound, 111196-81-7, name is 2-Chloro-5-ethylpyrimidine, molecular formula is C6H7ClN2, 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: In a reaction vial designed for microwave heating, the considered alkoxypyrazole (2 mmol), the considered halogenated heteroaryl (2.2 mmol) and cesium carbonate (2.8 mmol) were stirred in dimethylformamide or acetonitrile (3 mL) as specified in the examples. This was heated using a microwave at a temperature between 120 C and 180 C for the individually specified duration. The resulting suspension was diluted in water, extracted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate and concentrated to dryness. The residue was further purified as described below.

The synthetic route of 111196-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSTITUT PASTEUR; JANIN, Yves-Louis; GUILLOU, Sandrine; LUCAS-HOURANI, Marianne; MUNIER-LEHMANN, Helene; NOEL, Anne; SALANOUVE, Elise; TANGY, Frederic; VIDALAIN, Pierre-Olivier; WO2015/155680; (2015); A2;,
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