Tag: M.W=300-400

Synthetic Route of 153435-63-3, 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 153435-63-3, name is 2-(Tributylstannyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 3-8 (Trans)-8-[(2,5′-bipyrimidin-2′-Vlamino)methyl]-3-(2-pyridinyl)-1-oxa-3-azaspiro[4.5]decan-2-one To a solution of (trans)-8-{[(5-bromo-2-pyrimidinyl)amino]methyl}-3-(2-pyridinyl)-1-oxa-3-azaspiro[4.5]decan-2-one (Intermediate 24, 30 mg, 0.072 mmol) in dimethylsulfoxide (3 ml) 2-(tributylstannanyl)pyrimidine (26.5 mg, 0.072 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.32 mg, 2.87 mumol) were added and the resulting mixture was irradiated in a microwave oven at 120 C. for 10 min. The crude solution was first eluted on a SCX cartridge (DCM/MeOH/NH3 (2M soln in MeOH) 100/0/0 to 80/10/10) and evaporated to dryness. Purification by silica gel chromatography (SP1 automated instrument, SNAP 10 g Si cartridge, elution in gradient with 0%-10% MeOHDCM) gave the title compound as a white solid (15 mg, 0.036 mmol, 50%).

According to the analysis of related databases, 153435-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Biagetti, Matteo; Contini, Stefania Anna; Genski, Thorsten; Guery, Sebastien; Leslie, Colin Philip; Mazzali, Angelica; Pizzi, Domenica Antonia; Sabbatini, Fabio Maria; Seri, Catia; US2009/203705; (2009); A1;,
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

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

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

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

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. 58536-46-2, name is 4-(4-Bromophenyl)-2,6-diphenylpyrimidine, molecular formula is C22H15BrN2, 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. Safety of 4-(4-Bromophenyl)-2,6-diphenylpyrimidine

Under a nitrogen atmosphere 2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,10-phenanthroline (5.0 g, 13.08 mmol) 4- (4-bromophenyl) -2,6-diphenylpyrimidine (6.10 g, 15.96 mmol), tetrakis-triphenylphosphine palladium (0) (Pd (PPh3) 4) (0.75 g, 0.65 mmol) 4M potassium carbonate aqueous solution (10 mL), toluene 30 mL, ethanol 10 mL And the mixture was stirred under reflux for 12 hours. After the reaction was completed, 50 mL of H2O was added, and the mixture was stirred for 3 hours. The mixture was filtered under reduced pressure, separated by column chromatography using methylene chloride (MC) and methanol as an eluent, EN-145-1 (5.56 g, yield 75.6%).

With the rapid development of chemical substances, we look forward to future research findings about 58536-46-2.

Reference:
Patent; LG Display Co., Ltd.; Shin Ji-cheol; Joo Seong-hun; Ryu Seon-geun; Yoon Seung-hui; (44 pag.)KR2018/67321; (2018); A;,
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. 153435-63-3, name is 2-(Tributylstannyl)pyrimidine, the common compound, a new synthetic route is introduced below. Formula: C16H30N2Sn

38(a) ethyl N-{[6-hydroxy-7-(2-pyrimidinyl)-5-quinoxalinyl]carbonyl}glycinate. To a solution of ethyl N-[(7-bromo-6-hydroxy-5-quinoxalinyl)carbonyl]glycinate (0.120 g, 0.339 mmol) (prepared as in N2843-54-A1) in 1,4-dioxane (1.5 ml) was added 2-(tributylstannanyl)pyrimidine (0.138 g, 0.374 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.020 g, 0.017 mmol) followed by heating to 150 C. for 60 min. in a Biotage Initiator microwave synthesizer. Upon cooling, the reaction mixture was concentrated in vacuo and purified via flash column chromatography (0-100% ethyl acetate in hexane) to obtain ethyl N-{[6-hydroxy-7-(2-pyrimidinyl)-5-quinoxalinyl]carbonyl}glycinate (0.083 g, 0.235 mmol, 69.3% yield) as a pale orange solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 14.90 (s, 1H), 10.12 (t, J=5.8 Hz, 1H), 9.09 (s, 1H), 9.07 (s, 1H), 8.97 (d, J=1.8 Hz, 1H), 8.91 (d, J=2.0 Hz, 1H), 8.81 (s, 1H), 7.68 (t, J=4.9 Hz, 1H), 4.23 (d, J=5.8 Hz, 2H), 4.18 (q, J=7.2 Hz, 2H), 1.26 (t, J=7.2 Hz, 3H). MS (ES+) m/e 354 [M+H]+.

The synthetic route of 153435-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; US2010/305133; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1421372-94-2, N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine, 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 N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine, blongs to pyrimidines compound. Quality Control of N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine

Compound 6 (7.7 mL) was added to a suspension of N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methylindol-3-yl)pyrimidin-2-amine (compound 5, 15.5 g, 0.79) and K2CO3 (16.3 g) DMF (60 mL). The mixture was heated at 60 C. for 60 min and then water (150 mL) was added. Solids were filtered and rinsed with water. The crude dark red product was directly used in the next step without further purification.

The synthetic route of 1421372-94-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; X-Cutag Therapeutics, Inc.; CHENG, Changfu; WEN, Shuhao; LI, Hui Joyce; (30 pag.)US2019/169171; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 761440-16-8, 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 761440-16-8, name is 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

4-(4-Amino-5-isopropoxy-2-methyl-phenyl)-piperidine-l-carboxylic acid tert-butyl ester (170 mg, 0.488 mmol) from the previous step, (2,5-Dichloro-pyrimidin-4-yl)-[2-(propane- 2-sulfonyl)-phenyl]-amine (Intermediate 2, 169 mg, 0.488 mmol, 1 equiv.), xantphos (28 mg, 0.049 mmol, 0.1 equiv.), palladium acetate (5.5 mg, 0.024 mmol, 0.05 equiv.), and Cs2CO3 (477 mg, 1.46 mmol, 3 equiv.) are dissolved in anhydrous THF (6 mL). N2 is bubbled through the reaction mixture for 5 minutes and then the reaction vessel is sealed and heated with microwave irradiation to 150 0C for 20 min. The reaction is filtered and the filtrate concentrated under vacuum. After concentration, the crude product is purified by silica gel chromatography (gradient from hexanes to 30% ethyl acetate in hexanes) to give 4-(4-{5-chloro-4-[2-(propane-2- sulfonyl)-phenylamino]-pyrimidin-2-ylamino}-5-isopropoxy-2-methyl-phenyl)-piperidine-l- carboxylic acid tert-butyl ester as a yellow film: ESMS m/z 658.3 (M + H+). This product (105 mg, 0.160 mmol) is dissolved in CH2Cl2 (3 mL) and treated with TFA (3 mL). After 45 min., the reaction is concentrated under vacuum. 1 N HCl in Et2O (5 mL x 2) is added causing the product HCl salt to precipitate. The solvent is removed by decantation. The resulting 5- Chloro-N2-(2-isopropoxy-5-methyl-4-piperidin-4-yl-phenyl)-N4-[2-(propane-2-sulfonyl)- phenyl]-pyrimidine-2,4-diamine (66) is dried under high vacuum, generating an off-white powder: 1H NMR (400 MHz, DMSO-J6 + trace D2O) delta 8.32 (s, IH), 8.27 (d, IH), 7.88 (d, IH), 7.67 (dd, IH), 7.45 (dd, IH), 7.42 (s, IH), 6.79 (s, IH), 4.56-4.48 (m, IH), 3.49-3.32 (m, 3H), 3.10-2.91 (m, 3H), 2.09 (s, 3H), 1.89-1.77 (m, 4H), 1.22 (d, 6H), 1.13 (d, 6H); ESMS m/z 558.1 (M + H+).

According to the analysis of related databases, 761440-16-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; WO2008/73687; (2008); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 330786-24-8 ,Some common heterocyclic compound, 330786-24-8, molecular formula is C17H13N5O, 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.

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (120.00 mg, 395.62 mumol) was weighed in a single-mouth flask and anhydrous tetrahydrofuran (10 ml) was added. Triphenylphosphine (311.30 mg, 1.19 mmol), 2-fluoroethanol (25.34 mg, 395.62 mumol) and diethyl azodicarboxylate (239.99 mg, 1.19 mmol) were added under argon atmosphere at room temperature overnight. TLC monitoring The reaction is complete. The reaction solution was concentrated and column chromatography gave BTK-8 78.00 mg, yield 56.43%.

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. 330786-24-8, 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Institute of Technology; Yao Zhiyi; Yang Yan; Xia Xiaoming; Xue Nannan; Shu Qisheng; Wang Qingxuan; Wang Dongsheng; (7 pag.)CN107827892; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia