Month: March 2021

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
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. 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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13036-57-2, 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.13036-57-2, name is 2-Chloro-4-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

A solution of Lithium bis(trimethylsilyl)amide (1M in THF, 10.26mL, 10.26mmol) was added to a cooled (0C) solution of Methyl 3-((tert-butoxycarbonyl)amino)-2- fluorobenzoate (790mg, 2.93mmol) in THF (15mL). After lOmin of stirring, a solution of 2-chloro-4-methylpyrimidine (452mg, 3.52mmol) in THF (2mL) was slowly added and the reaction mixture was allowed to warm to 40C for lh. Aqueous saturated ammonium chloride was added to the medium. The aqueous layer was extracted with EtOAc (2 times). Combined organics were washed with brine, dried over sodium sulphate, filtered and the filtrate was concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel (cHex-EtOAc 1/0 to 0/1) afforded the title compound (880mg, 82%). LC/MS (ES+): 366.3-368.3 (M+l).

Statistics shows that 13036-57-2 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-4-methylpyrimidine.

Reference:
Patent; CELLIPSE; PRUDENT, Renaud; PAUBLANT, Fabrice; (74 pag.)WO2018/55097; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 7752-82-1, 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. 7752-82-1, name is 5-Bromopyrimidin-2-amine. A new synthetic method of this compound is introduced below.

A mixture of 5-bromo-pyrimidin-2-ylamine (0.8g, 4.59mmol), 4-bromophenyl boronic acid(1g, 4.97mmol), tetrakis(triphenylphosphine)palladium(0) (3OOmg, 0.259mmol), cesium carbonate (1.15g, 3.03mmol) was stirred in MeOH/H2O (20ml, 1/1 ) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200ml) and water (50ml). The organic layer was separated, dried over MgSO4, filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 85% v/vEtOAc/hexanes yielding product 81 as white solid. (0.7g, 63%). ESMS (MH, 250).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7752-82-1, 5-Bromopyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2008/156739; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. Safety of Ethyl 2-chloropyrimidine-5-carboxylate

Example 1 Synthesis of 2-(diphenylamino)-N-(7-(hydroxyamino)-7-oxoheptyl) pyrimidine-5-carboxamide (Compound A) Synthesis of Intermediate 2 A mixture of aniline (3.7 g, 40 mmol), ethyl 2-chloropyrimidine-5-carboxylate 1 (7.5 g, 40 mmol), K2CO3 (11 g, 80 mmol) in DMF (100 ml) was degassed and stirred at 120 C. under N2 overnight. The reaction mixture was cooled to rt and diluted with EtOAc (200 ml), then washed with saturated brine (200 ml*3). The organic layer was separated and dried over Na2SO4, evaporated to dryness and purified by silica gel chromatography (petroleum ethers/EtOAc=10/1) to give the desired product as a white solid (6.2 g, 64%).

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

Reference:
Patent; Acetylon Pharmaceuticals, Inc.; Quayle, Steven Norman; Jones, Simon Stewart; Anderson, Kenneth C.; Hideshima, Teru; US2015/105358; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, molecular formula is C5H4Cl2N4O, 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: N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide

To a slurry of N-(2-amino-4,6-dichloro-5-pyrimidinyl) formamide (42g) in 2- propanol (500 ml), triethylamine (31.4g) was added at 230C. The slurry was heated to 75-8O0C. A solution of 4-amino-2-hydroxymethylbutan-l-ol (27gm, -95% purity) in a mixture of 2-propanol (120ml) and water (17.4 ml) was slowly added to the refluxing reaction mass in about 60 minutes. The mixture was stirred at 75-8O0C for 2 hrs for completion of the reaction and concentrated under reduced pressure. The resulting residue was diluted with methanol (900 ml) and treated with activated charcoal (2 g). The solution was filtered through celite and the residue was washed with methanol (80 ml). To the filtrate 10% Palladium on Carbon (50% water paste, 6g) was added. The slurry was transferred to a hydrogenation vessel and hydrogenated at ~50C and 5-6 kg/cm2 for 20 hrs. After completion of the reaction, catalyst was removed by filtration and the residue washed with methanol (50 ml). The combined filtrate was concentrated to ~130 ml under reduced pressure at < 5O0C. The concentrate was cooled to -230C and hydrogen chloride solution in methanol (54gm, 17% w/w) was added. The light yellow coloured solution was stirred for 5-10 minutes at -230C and trimethylorthoformate (96.8Og) was added. The solution was heated to about 450C and continued stirring at 45-5O0C for 4 hrs. Thereafter, a mixture of 4gm concentrated hydrochloric acid and 6 g water was added. Stirring was continued at 45-5O0C for 90 minutes, product start crystallizing after 20 minutes of stirring. The suspension was cooled to 5-80C, stirred for 60 minutes. Product was filtered and washed with prechilled methanol (30ml, O0C), and dried at 5O0C under reduced pressure to constant weight yield 27.4 g: off white powder, HPLC purity > 98.1%.

With the rapid development of chemical substances, we look forward to future research findings about 171887-03-9.

Reference:
Patent; AUROBINDO PHARMA LIMITED; WO2008/72074; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 20737-41-1, 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 20737-41-1, name is 4-Aminopyrimidine-5-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

(Step 1) Methyl 4-aminopyrimidine-5-carboxylate (0191) (0192) 4-Aminopyrimidine-5-carboxylic acid (10.0 g, 71.9 mmol) was dissolved in methanol (100 ml), the reaction solution was cooled to 0 C., then concentrated sulfuric acid (25 ml) was slowly added dropwise, and the resulting mixture was stirred at 85 C. for 12 hours. The reaction liquid was concentrated under reduced pressure, then the resulting solution was diluted with water, and sodium hydrogen carbonate (10.0 g) was added. The resulting mixture was extracted with ethyl acetate (80 ml¡Á4), the extracts were combined, washed with a saturated saline solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, the obtained residue was stirred in a mixed solvent (petroleum ether:ethyl acetate=8:1), and the precipitated solid was filtered and dried to obtain the title compound (9.90 g, 90%). (0193) 1H-NMR (400 MHz, DMSO-d6): delta 8.72 (s, 1H), 8.53 (s, 1H), 8.04 (s, 1H), 7.62 (s, 1H), 3.83 (s, 3H); MS (ESI) m/z 154 (M+H)+

According to the analysis of related databases, 20737-41-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ajinomoto Co., Inc.; UENO, Hirokazu; YAMAMOTO, Takashi; MIYAZAWA, Tomoko; SHINKAI, Kenji; ARISAKA, Harumi; TAKANOHASHI, Toshiyuki; (122 pag.)US2016/244451; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 10070-92-5, 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. 10070-92-5, name is Pyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below.

A mixture of the product from Preparative Example 28 (1.16 g, 4.00 mmol), pyrimidine-5-carboxaldehyde (540 mg, 5.00 mmol), and Ti(OiPr)4 (4.54 g, 16.0 mmol) in anhydrous THF (20 mL) was stirred under N2 at 50 C. for 3 hr. The mixture was cooled to 25 C., NaBH3CN (1.26 g, 20.0 mmol) was added, and the mixture was stirred at 25 C. for 30 min. The mixture was poured into 5% aqueous NaOH (500 mL), saturated aqueous NaCl (50 mL) was added, and the mixture was extracted with CH2Cl2 (3¡Á100 mL). The combined extracts were dried over Na2SO4, filtered, and the solvent was evaporated. The residue was purified by column chromatography on silica gel with CH2Cl2/MeOH/conc. aqueous NH4OH (20:1:0.1). Pale yellow solid (410 mg, 27%) was obtained. M. P. 201-203 C., LCMS: MH+=383.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10070-92-5, Pyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; US2004/63715; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia