Month: April 2021

Related Products of 18740-39-1, 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. 18740-39-1, name is 2,4-Dichlorothieno[2,3-d]pyrimidine, molecular formula is C6H2Cl2N2S, 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.

General procedure: To a solution of 2,4-dichloro-5-fluoroquinazoline (22a) (100.00mg, 460.77 mumol, 1.00 eq) in THF (3.00mL) was added methyl (2S,3S)-3-aminobicyclo[2.2.2]octane-2-carboxylate (84.44mg, 460.77 mumol, 1.00 eq) and DIPEA (238.20mg, 1.84mmol, 4.00 eq) at room temperature overnight. H2O (20mL) was added to the mixture and extracted with EtOAc (10mL¡Á3). The combined organic layers were dried over Na2SO4 and concentrated in vacuum. The residue was purified by column chromatography on silica gel with PE:EtOAc (10:1 to 5:1) to give compound 23a (130.00mg, 357.33 mumol, 77.55% yield) as a yellow solid.

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 18740-39-1, 2,4-Dichlorothieno[2,3-d]pyrimidine.

Reference:
Article; Xiong, Jian; Wang, Jingjing; Hu, Guoping; Zhao, Weili; Li, Jianqi; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 249 – 265;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 183438-24-6, 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. 183438-24-6, name is 5-Bromo-2-iodopyrimidine, molecular formula is C4H2BrIN2, 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.

5-Bromo-2-iodopyrimidine (2 g, 7.02 mmol) was dissolved in dry toluene (30 mL) and cooled to -78 C under nitrogen. A 2.5M solution of n-BuLi in hexane (2.95 mL) was added drop wise and the reaction stirred for 15 minutes prior to the drop wise addition of tetrahydro-4H-pyran-4-one (0.77 g, 7.72 mmol). The reaction was stirred at -78 C for 30 min and then was allowed to warm to r.t.. The reaction mixture was diluted with water – -(50 mL) and extracted with EtOAc (2 x 50mL). The combined organic extracts were dried over magnesium sulfate and the solvent removed under reduced pressure to afford 1.9 lg of crude product as an orange oil. The crude orange oil was purified by flash column chromatography (Si02, 10-100% EtOAc in heptane) to afford 762 mg (42 %) of the title compound as a yellow oil.1H NMR (500 MHz, CDC13) delta ppm 8.79 (s, 2H), 4.24 (s, 1H), 3.99 – 3.89 (m, 4H), 2.37 (td, J 12.3, 11.6, 6.3 Hz, 2H), 1.54 (dd, J 13.6, 2.0 Hz, 2H).

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 183438-24-6, 5-Bromo-2-iodopyrimidine.

Reference:
Patent; UCB BIOPHARMA SPRL; ALEXANDER, Rikki, Peter; BRACE, Gareth, Neil; BROWN, Julien, Alistair; CALMIANO, Mark, Daniel; CHOVATIA, Praful, Tulshi; DELIGNY, Michael; GALLIMORE, Ellen, Olivia; HEER, Jag, Paul; JACKSON, Victoria, Elizabeth; KROEPLIEN, Boris; MAC COSS, Malcolm; QUINCEY, Joanna, Rachel; SABNIS, Yogesh, Anil; SWINNEN, Dominique, Louis, Leon; ZHU, Zhaoning; WO2015/86526; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1193-24-4, 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 1193-24-4, name is 4,6-Dihydroxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

With a reflux condenser, thermometer,In the device of the agitator and the constant pressure dropping funnel,Add 4,6-dihydroxypyrimidine (114.3 g, content 98%, 1 mol), phosphorus oxychloride (1140 g, 99%) and mix well.The temperature was raised to 95-100 C, and phosgene (220 g, 99%, 2.2 mol) was slowly added to carry out the reaction, and the sample was taken after 8 hours.HPLC analysis of 4,6-dihydroxypyrimidine content of 0.9%,The content of 4,6-dichloropyrimidine was 98.3%, and the reaction was over.Vacuum distillation reaction mixture (oil bath temperature 95 C,Vacuum degree -0.095MPa),Obtained 1082 g of phosphorus oxychloride (content 99%); 142.8 g of 4,6-dichloropyrimidine (content 99.0%),Yield 94.9% (based on 4,6-dihydroxypyrimidine), wherein W (DCP) refers to the mass of DCP, and W (DHP) refers to the mass of DHP.The content refers to the mass content of DCP, and 112 is the molecular weight of DHP.149 is the molecular weight of DCP.

According to the analysis of related databases, 1193-24-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lianyungang Guosheng Chemical Co., Ltd.; Xu Chen; Zhu Guoqing; Zhang Xin; Zhou Tulin; (6 pag.)CN108178749; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.50593-92-5, name is 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid, molecular formula is C6H5BrN2O2S, molecular weight is 249.09, as common compound, the synthetic route is as follows.Safety of 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid

A catalytic amount of N,N-dimethylformamide (2 drops) was added to a stirred suspension of 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (2.07 g, 8.33 mmol) and a 2 M solution of oxalyl chloride (21 mL, 0.042 mol) in dichloromethane under nitrogen at r.t. Vigorous effervescence was observed. After 30 min everything had dissolved and the solvent was then evaporated in vacuo. The residue was dissolved in dichloromethane (20 mL) and placed under nitrogen. Triethylamine (2.32 mL, 16.66 mmol) was added to this stirred solution at r.t. followed by 4-aminopyridin-3-yl diethylcarbamodithioate (2.01 g, 8.33 mmol). Everything quickly dissolved with a noticeable exotherm. After 3 h at r.t. tic showed a new major product. The reaction was diluted with dichloromethane (20 mL) and washed with a saturated aqueous solution of sodium hydrogen carbonate (40 mL). The organic layer was separated, dried over sodium sulfate, filtered and the solvent evaporated in vacuo. The residue was purified by flash chromatography (ethyl acetate / hexane 15:85 to 60:40) to yield 4-(5-bromo-2- (methylthio)pyrimidine-6-carboxamido)pyridin-3-yl diethylcarbamodithioate (1.99 g, 51%) as a pale yellow amorphous solid. 1H NMR : delta (CDCl3, 400 MHz) 1.30 (t, J = 7 Hz, 3 H), 1.51 (t, J= 7 Hz, 3 H), 2.60 (s, 3 H), 3.93 – 4.08 (m, 4 H), 8.57 – 8.62 (m, 2 H), 8.69 (d, J = 6 Hz, 1 H), 8.85 (s, 1 H), 10.67 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,50593-92-5, 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN, INC.; WO2006/66172; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 767-15-7, 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. 767-15-7, name is 2-Amino-4,6-dimethylpyrimidine. A new synthetic method of this compound is introduced below.

2-Amino-5-bromo-4,6-dimethylpyrimidine (3):; To a stirred solution containing 4.3 lg (34.75 mmol) of 2-amino-4,6-dimethylpyrimidine (2) in 150 mL of acetonitrile were added 6.15g (52.12 mmol) of N-bromosuccinimide. The reaction mixture was stirred at room temperature under argon atmosphere for 3 h. The formed precipitate was filtered and dried to afford the expected product as a white solid: yield 5.93g (83%).1H-NMR(CDC13) delta 5.19 (br, 2H), 2.44 (s, 6H);13C-NMR (CDC13) delta 166.28, 160.73, 109.60, 24.70.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,767-15-7, 2-Amino-4,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ARIZONA BOARD OF REGENTS; HECHT, Sidney; ARMSTRONG, Jeffrey; KHDOUR, Omar; LU, Jun; ARCE, Pablo; WO2011/103536; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 131860-97-4, 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 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. This compound has unique chemical properties. The synthetic route is as follows.

Further screening experiments, using DMF as a solvent, were carried out as detailed below: Methyl (?)-2-{2-[6-chlororhoyrimidin-4-yloxy]ph.enyl}-3-methoxyacrylate (H) (6.4g of 45.2% strength solution in DMF) was charged to the reaction tube followed by further DMF (6.4 g), 2-cyanophenol (1.2g), potassium carbonate (1.5 mol equivalents) and the compound being tested as a catalyst (10 mol%). The reaction mixtures were held, with stirring, at 4O0C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for loss of starting material and formation of product, throughout the hold periods, by Gas Chromatography. Results are recorded as area % levels of methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3- methoxyacrylate (II) and methyl (2s)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3- methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE 3The results are shown in Table 4 below:; A stirred solution of (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (80.Og at 98%w/w, 0.24mols) in DMF (8Og) was heated to approximately 60C and then potassium carbonate (51.6g at 98%w/w, 0.37mols), 2-cyanophenol (32.8g at 97.5%w/w, 0.27mols) in DMF (32.8g) and quiniclidinone hydrochloride (2.03g at 97%w/w, 0.012mols were added at five minute intervals. The reaction mixture was heated to 800C and held at this temperature for 195 minutes when analysis indicated that the reaction was complete. The DMF was distilled off under vacuum to a final temperature of 100C and then toluene (134.8g) was charged, followed by hot water (259.4g), maintaining the temperature of the mixture above 7O0C. The mixture was stirred at 80C for 30 minutes, settled and then the aqueous phase separated. The toluene phase (226.4g) contained methyl (E)-2- {2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (41.58%w/w) 95.8% of theory.

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 131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43977; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 761440-16-8 , The common heterocyclic compound, 761440-16-8, name is 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine, molecular formula is C13H13Cl2N3O2S, 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 500L enamel reactor was added 80.6kg of isopropanol,12.4 kg of the compound 1-dihydrochloride obtained in Example 1 and 14.7 kg of the compound 3 obtained in Example 6,Heated to reflux, the reaction 24 hours. The reaction solution was cooled to 10 C, stirred for 3 hours,filter.The wet filtered product was added enamel reactor,99.2 kg of isopropanol and 13.0 kg of purified water were added,Reflux stir until solids are clear.Control temperature not lower than 85 ,99.2 kg of isopropanol was added dropwise.Slowly cooled to 20 ,Stir for 2 hours and filter.The wet filtered product was added to the enamel reactor again,Add 99.2 kg of isopropanol and 13.0 kg of purified water and stir under reflux until the solid is clear.Controlled at a temperature not lower than 85 C, 99.2 kg of isopropanol was added dropwise.Slowly cooled to 20 C, stirred for 2 hours, filtered, washed with isopropanol.The filtered wet product was vacuum dried at 55 C for 16 hours,A 16.4 kg yellow solid (Compound 4, ceritinib dihydrochloride) was obtained in a yield of 67% and a purity of 99.9%.

The synthetic route of 761440-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Xingtai Pharmaceutical Technology Co., Ltd.; Liu Xuejun; Hong Huiyi; Chen Xiaodong; (12 pag.)CN106854200; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.1202759-91-8, name is N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine, molecular formula is C19H20FN5O2, molecular weight is 369.3928, as common compound, the synthetic route is as follows.category: pyrimidines

Weigh 29mgMonomethyl fumarate,84mg HATU, 30mg HOAT in a 25ml round bottom flask, add 1.6mlDCM, 0.4 ml DMF and 66 mul DIEA were used as solvents. After stirring at room temperature for about 10 minutes, 74 mg of the A1 intermediate was added to the reaction system. After stirring for about 1 hour at room temperature, 100 ml of saturated aqueous sodium bicarbonate solution was added, followed by 15 ml of DCM. The mixture was extracted 3 times and the organic phase was evaporated to dryness under reduced pressure. The residue was applied to a silica gel column with DCM_MeOH=70:1 (volume ratio) to obtain 60 mg of the compound represented by Formula I-2 in a yield of 62%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1202759-91-8, N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Tsinghua University; Rao Yu; Liu Wanli; Yang Maojun; Sun Yonghui; (22 pag.)CN107973754; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 6328-58-1, Adding some certain compound to certain chemical reactions, such as: 6328-58-1, name is 6-Methyl-2-(methylthio)-1H-pyrimidin-4-one,molecular formula is C6H8N2OS, 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 6328-58-1.

Propargyl bromide (2) (1.2 mmol, 0.10 mL) was added slowlyto a stirred mixture of 6-methyl-2-(methylthio)pyrimidine-4(3H)-one (1) (1.0 mmol, 0.15 g) and K2CO3 (2.0 mmol,0.27 g) in dry DMF (4 mL) at room temperature, and the mixturewas stirred at room temperature for 10 h. Upon completionof the reaction, the solvent was evaporated under vacuum,and the resulting residue was washed with water. The residuewas finally purified by flash column chromatography (hexane/ethyl acetate = 10:1) to give the titles compounds. Compound (3): TLC (hexane/ethyl acetate = 10:1)Rf = 0.7; yield 70%; white powder; m.p. 80-82 C; 1H NMR(300 MHz, CDCl3): delta 2.38 (s, 3H, CH3), 2.51 (t, J = 2.4 Hz,1H, CH), 2.56 (s, 3H, CH3), 5.00 (d, J = 2.4 Hz, 2H, CH2),6.30 (s, 1H, ArH); 13C NMR (75 MHz, CDCl3): delta 14.0,23.8, 53.6, 74.9, 78.1, 102.0, 167.9, 168.1, 171.3; IR (KBr):3167, 2925, 2116, 1581, 1404, 1339, 1041 cm-1. Anal.calcd for C9H10N2OS: C, 55.65; H, 5.19; N, 14.42; found:C, 55.82; H, 5.28; N, 14.58%.Compound (4): TLC (hexane/ethyl acetate = 10:1) Rf = 0.52;yield 30%; white powder; m.p. 122-124 C; 1H NMR(300 MHz, CDCl3): delta 2.15 (s, 3H, CH3), 2.20 (t, J = 2.4 Hz, 1H,CH), 2.53 (s, 3H, CH3), 4.76 (d, J = 2.4 Hz, 2H, CH2), 6.00(s, 1H, ArH); 13C NMR (75 MHz, CDCl3): delta 15.1, 23.8, 32.6,72.3, 107.6, 161.1, 161.3, 162.7; IR (KBr): 3124, 3001, 1645,1581, 1543, 1461 cm-1. Anal. calcd for C9H10N2OS: C, 55.65;H, 5.19; N, 14.42; found: C, 55.79; H, 5.11; N, 14.28%.

According to the analysis of related databases, 6328-58-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rezaeimanesh, Fatemeh; Bakherad, Mohammad; Nasr-Isfahani, Hossein; Journal of Chemical Research; vol. 43; 9-10; (2019); p. 431 – 436;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 374930-88-8, 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.374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, molecular formula is C13H19BrN4O2, molecular weight is 343.2196, as common compound, the synthetic route is as follows.

General procedure: In a dried microwave reactor vessel were added 3-bromoquinoline(0.204 mL, 1.5 mmol), Pd(dba)2 (86 mg, 0.15 mmol), K2CO3carbonate (415 mg, 3.00 mmol), S-Phos (185 mg, 0.45 mmol), dryD8-IPA (0.500 mL) and MeCN (1 mL). The mixture was degassedand placed under a nitrogen atmosphere. The sealed reaction tubewas heated to 100 C in a microwave (Biotage Initiator) for 2.5 h.The solvents were removed under reduced pressure, the crudematerial pre-loaded on to silica and purified using flash silica chromatography(15% EtOAc/heptane). The fractions containing thedesired compound were combined and evaporated to dryness toafford 3-deuterioquinoline (140 mg, 72%); 1H NMR (400 MHz,DMSO, 27 C): d (ppm) 7.62 (ddd, J = 1.20, 6.89, 8.11 Hz, 1H), 7.77(ddd, J = 1.50, 6.87, 8.43 Hz, 1H), 7.99 (dd, J = 1.33, 8.18 Hz, 1H),8.03 (d, J = 8.41 Hz, 1H), 8.37 (s, 1H), 8.91 (d, J = 1.70 Hz, 1H); 13CNMR (176 MHz, DMSO, 30 C) 121.0, 126.4, 127.8, 128.0, 128.8,129.3, 135.8, 147.7, 150.3; HRMS (EI): M+, found 130.0643,C9H6DN requires 130.0641.

The chemical industry reduces the impact on the environment during synthesis 374930-88-8, I believe this compound will play a more active role in future production and life.

Reference:
Article; Donald, Craig S.; Moss, Thomas A.; Noonan, Gary M.; Roberts, Bryan; Durham, Emma C.; Tetrahedron Letters; vol. 55; 22; (2014); p. 3305 – 3307;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia