Pyrimidines

Reference of 289042-12-2, 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. 289042-12-2, name is tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate, molecular formula is C29H40FN3O6S, 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.

To a solution of compound IV (wherein X=0 and R2=tert-butyl; 100 gms) in acetonitrile (700 mL) at 35C to 40C was added 0.05M aqueous HCl solution (300 mL). Stirred the reaction mass at 35C to 40C until reaction completion and cooled to 0C to 5C. Added 1.0 M aqueous sodium hydroxide solution (300 mL), temperature was raised to 25 C to 35C and stirred until reaction completion. Cooled the reaction mass to 0C to 5C, pH was adjusted to 3.4 to 4.0 with 1M aqueous HCl solution (300 mL) and extracted with ethyl acetate. Washed the organic layer with 10% aqueous sodium chloride solution and concentrated under vacuum. Charged ethyl acetate (800 mL) to the obtained residue followed by cyclohexane- 1,2-diamine (29.5 gms) over a period of 15-30 min. The reaction mass was stirred at 25C to 35C for 60 mins, cooled to 0C to 5C and stirred for 2 hrs. The precipitated product was filtered and dried to obtain 80 gms of rosuvastatin cyclohexane- 1,2-diamine salt as white solid. HPLC Purity: >99% The XRPD is set forth in Figure 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 289042-12-2, tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate.

Reference:
Patent; LAURUS LABS PRIVATE LIMITED; BOLLU, Ravindra Babu; MANDADAPU, Venkata Pramod Kumar; INDUKURI, Venkata Sunil Kumar; GORANTLA, Seeta Rama Anjaneyulu; CHAVA, Satyanarayana; (48 pag.)WO2016/125086; (2016); A1;,
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Pyrimidine – Wikipedia

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. 56844-12-3, name is 6-Bromo-4-chlorothieno[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromo-4-chlorothieno[2,3-d]pyrimidine

General procedure: 6-Bromo-4-chlorothieno[2,3-d]pyrimidine(5a) (200 mg, 0.802 mmol) was mixed with 1-phenylethanol (2a) (118 mg, 0.962 mmol), Cs2CO3( 313 mg, 0.962 mmol) and acetonitrile (2 mL). The reaction was then stirredunder nitrogen atmosphere at reflux and followed by GC. The mixture was cooledto rt, diluted with EtOAc (40 mL), washed with sat. aq. KHCO3 (20mL), water (2×20 mL) and brine (30 mL). The combined organic fractions weredried over Na2SO4 and concentrated in vacuum. Crudeproduct was absorbed onto Celite 545 and purified by silica gel columnchromatography (n-pentane/EtOAc,6/1). This gave 245 mg (0.730 mmol, 91%) of 6a as an off-white solid.

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, 56844-12-3, 6-Bromo-4-chlorothieno[2,3-d]pyrimidine.

Reference:
Article; Han, Jin; Sundby, Eirik; Hoff, Bage H.; Journal of Fluorine Chemistry; vol. 153; (2013); p. 82 – 88;,
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Application of 63558-65-6, 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. 63558-65-6, name is 4-Chloro-5-iodopyrimidine, molecular formula is C4H2ClIN2, 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.

Step 4: 6-Chloro-3′-[(5-iodopyrimidin-4-yl)amino]-N-[3-(trifluoromethyl)phenyl]biphenyl-3- carboxamideIn a screw-capped vial, 3′-amino-6-chloro-lambda^-[3-(trifluoromethyl)phenyl]biphenyl-3- carboxamide (240 mg TFA salt, 0.476 mmol) was mixed with 4-chloro-5-iodopyrimidine (0.131 g, 0.543 mmol) and isopropyl alcohol (2.0 mL), and the mixture was heated to 80 0C. After 16 h, the reaction was complete by LCMS (M+H 595/597, 3: 1). To the reaction mixture was added potassium carbonate solution. The resulting mixture was extracted with ethyl acetate and the organic extracts were washed with water, and then with saturated NaCl, and then dried (Na2SOzO and concentrated in vacuo to provide a residue (0.3g). TLC (30% EtOAc-hexane) Rf 0.19. The residue was purified by automatic flash chromatography on silica gel using a 12 g column; flow 30 mL/min; [A= hexane] [B= EtOAc ]. A, 4 min; Gradient to 30% B in 30 min. The product eluted in 26-32 min and the fractions were concentrated to give 0.19g of the purified product.

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 63558-65-6, 4-Chloro-5-iodopyrimidine.

Reference:
Patent; INCYTE CORPORATION; WO2008/79965; (2008); A1;,
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Reference of 5767-35-1, 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. 5767-35-1, name is 4-Chloro-6-hydrazinopyrimidine. A new synthetic method of this compound is introduced below.

General procedure: To the suspension of appropriate 1-(6 -chloropyrimidin chloropyrimidin-4-yl) (3) (3.0 mmol) in EtOH (15 mL) was added dropwise with vigorous stirring an aldeldehyde (3.6 mmol, 1.2 equiv) at rt over 0.5-1 h. The progression of the reaction was monitored by TLC. After completion of the reaction, solvent was removed under reduced pressure to afford the crude product. Crystallization from an appropriate solvent or purification by column chromatography on silica gel furnished the pure hydrazones 4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5767-35-1, 4-Chloro-6-hydrazinopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Tang, Caifei; Li, Zhiming; Wang, Quanrui; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 2629 – 2634;,
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Electric Literature of 23945-44-0 ,Some common heterocyclic compound, 23945-44-0, molecular formula is C5H4N2O4, 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.

To 10.0 g (64.06 mmol) of uracil-5-carboxylic acid (Aldrich Chemical Company) partially dissolved in 20 mL of DMF are added, under cold conditions, 59.7 mL (0.64 mol) of phosphorus oxychloride and 10.3 mL (64.7 mmol) of N,N-diethylaniline, and the mixture is then heated at 90° C. for 2 hours 40 minutes.After cooling to room temperature and evaporating off half the excess POCl3, the medium is poured onto ice and then extracted with ether.The ether phases are combined, dried over sodium sulfate, filtered and concentrated under vacuum. 8.1 g (41.97 mmol) of 2,4-dichloro-5-pyrimidinecarboxylic acid are obtained in a yield of 65percent.

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. 23945-44-0, 2,4-Dihydroxypyrimidine-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI; US2012/277220; (2012); A1;,
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Pyrimidine – Wikipedia

Related Products of 5334-35-0, 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 5334-35-0, name is 6-Chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Example 110 1 -methyl-6-(4-methylsulfonyl- 1 -piperidyl)-5H-pyrazolo[3 4-d]pyrimidin-4-one (1-141) The title compound was prepared by condensation (DIPEA/EtOH) of 4-methylsulfonyl- piperidine (CASRN 290328-55-1) and Intermediate A: 1H-NMR (400MHz, DMSO-i ) delta ppm 10.97 (s, 1H), 7.77 (s, 1H), 4.49 (d, J = 16.0Hz, 2H), 3.73 (s, 3H), 3.43-3.35 (m, 1H), 3.03-2.95 (m, 5H), 2.09 (d, J = 11.2Hz, 2H), 1.65-1.55 (m, 2H).

According to the analysis of related databases, 5334-35-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Jianwen; HAYNES, Nancy-Ellen; HERMANN, Johannes Cornelius; KIM, Kyungjin; LIU, Jin-Jun; SCOTT, Nathan Robert; YI, Lin; ZAK, Mark; ZHAO, Guiling; WO2013/182546; (2013); 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. 1546-78-7, name is 4-Hydroxy-6-(trifluoromethyl)pyrimidine, the common compound, a new synthetic route is introduced below. COA of Formula: C5H3F3N2O

To a solution of BE-1 (40.0 g, 244 mmol) in THF (800 mL) is added PPh3 (98.0 g) and NCS (160.0 g). The reaction mixture is stirred at 80 C for 10 h. The mixture is then quenched with water and extracted with EtOAc. The solution is concentrated and the residue is purified by Si02 flash chromatography to yield BE-2.

The synthetic route of 1546-78-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BAKONYI, Johanna; BRUNETTE, Steven Richard; COLLIN, Delphine; HUGHES, Robert Owen; LI, Xiang; LIANG, Shuang; SIBLEY, Robert; TURNER, Michael Robert; WU, Lifen; ZHANG, Qiang; WO2015/160654; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3435-25-4, 4-Chloro-6-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, 3435-25-4, blongs to pyrimidines compound. name: 4-Chloro-6-methylpyrimidine

General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. ‘H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (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,3435-25-4, its application will become more common.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; SHI, Dongchuan; KULTGEN, Steven G.; MCGUINNESS, Brian F; LETOURNEAU, Jeffrey J.; COLE, Andrew G.; BEASLEY, James R.; (358 pag.)WO2018/5801; (2018); 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. 24391-41-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, molecular formula is C7H3ClN4, 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. category: pyrimidines

To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (100 mg, 0.56 mmol, 1.00 equiv) in t-BuOH (15 mL) was added trans -N,N-dimethylcyclohexane-l,4-diamine (360 mg, 1.67 mmol, 3.0 equiv) and Et3N (3 ml). The resulting solution was stirred overnight at 100C in an oil bath. The resulting mixture was concentrated under vacuum and the residue was purified by Flash-Prep-HPLC with the following conditions: Column, SunFire Prep CI 8, 19* 150mm 5um; mobile phase, water with 0.05% NH4HC03 and CH3CN (8.0% CH3CN up to 65.0% in 14 min); Detector, 254/220nm. This resulted in 20.0 mg of 4-((-4- (dimethylamino)cyclohexyl)amino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile as white solid. LCMS: (ES, m/z): 285[M+H]+ 1H NMR-(300 MHz, CD3OD, ppm): delta 8.22 (1H, d), 7.81 (1H, s), 3.95-4.05 (1H, m), 2.30-2.40 (7H, m), 2.23-2.29 (2H, m), 1.95-2.05 (2H, m),1.30-1.50 (4H, m).

With the rapid development of chemical substances, we look forward to future research findings about 24391-41-1.

Reference:
Patent; NIMBUS IRIS, INC.; HARRIMAN, Geraldine C.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; WESSEL, Matthew David; GREENWOOD, Jeremy Robert; WO2014/11911; (2014); A2;,
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Pyrimidine – Wikipedia

Reference of 4983-28-2, Adding some certain compound to certain chemical reactions, such as: 4983-28-2, name is 2-Chloro-5-hydroxypyrimidine,molecular formula is C4H3ClN2O, 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 4983-28-2.

(Reference Example 12) 5-[(tert-Butyldimethylsilyl)oxy]-2-chloropyrimidine To a solution of 20.2 g (0.154 mol) of 2-chloro-5-hydroxypyrimidine in 150 ml of N,N-dimethylformamide, 15.8 g (0.232 mol) of imidazole and 26.8 g (0.178 mol) of tert-butyldimethylsilyl chloride were added, and the reaction mixture was stirred at room temperature for 2.5 hours. After completion of the reaction, the reaction solution was poured into water and extracted with n-heptane three times. The obtained organic phases were combined, washed with 0.01 N sodium hydroxide aqueous solution, water and saturated sodium chloride aqueous solution in order and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to provide 39.5 g of the title compound as a white solid (yield: 100percent). 1H-NMR spectrum (300 MHz, CD2 Cl2) delta: 8.21 (2H, s), 1.00 (9H, s), 0.25 (6H, s). Mass spectrum (EI, m/z): 244 [M+].

According to the analysis of related databases, 4983-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Daiichi Sankyo Company, Limited; UBE Industries, Ltd.; KAWAI, Yukinori; IWASE, Noriaki; KIKUCHI, Osamu; TAKATA, Katsunori; MOTOYAMA, Takahiro; HAGIHARA, Masahiko; EP2801574; (2014); A1;,
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Pyrimidine – Wikipedia