Day: July 28, 2021

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.2435-50-9, name is Pyrimidine-4-carbaldehyde, molecular formula is C5H4N2O, molecular weight is 108.0981, as common compound, the synthetic route is as follows.Formula: C5H4N2O

To a solu tion of e thyl (S)-2-((S)-pyrrolidine-2- carboxamido)-9-(5,6,7,8-tetrahydro-l,8-naphthyridin-2-yl)nonanoate (50 mg, 0.08 mmol, 1 equiv) in 0.5 mL MeOH was added pyrimidine-4-carbaldehyde (0.018 mL, 0.19 mol, 2.5 equiv). The mixture was heated at 40 C for 10 min before adding sodium cyanoborohydride (12 mg, 0.19 mmol, 2 5 equiv) and continuing to heat for an additional 2 h. The crude mixture was used directly in the next step

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2435-50-9, Pyrimidine-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; PLIANT THERAPEUTICS, INC.; LEFTHERIS, Katerina; REILLY, Maureen; FINKELSTEIN, Darren; COOPER, Nicole; BAILEY, Christopher; CHA, Jacob; (0 pag.)WO2020/6315; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1780-33-2, 4,6-Dichloro-2,5-dimethylpyrimidine, 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, SDS of cas: 1780-33-2, blongs to pyrimidines compound. SDS of cas: 1780-33-2

Two solutions, one with the aryl halide (0.56 mmol, 1.0 equivalent) in THF- H2O (2.5 mL, 3:2 v/v) and one with phenol (0.84 mmol, 1.5 equivalent) and NaOH (0.84 mmol, 1.5 equivalent) in THF-H2O (2.5 mL, 3:2 v/v) were prepared and then introduced into Asia microfluidic reactor by Pump A & B (see, e.g., Figure 4). The mixture was pumped through a preheated 1 mL glass microfluidic reactor at a predetermined flow rate to achieve the desired residence time. The crude product was collected in a flask and extracted with ethyl acetate. The organic phase was combined, dried MgSO4 and concentrated under reduced pressure. The isolated crude product was purified using a prepacked silica cartridge on a Teledyne CombiFlash Rf 200 instrument. Fractions corresponding to the product peak were combined and concentrated using rotavap to afford 1 as white solid (135 mg, 87percent).1H NMR (CDC13) delta2.08 (s, 3H), 2.36 (s, 3H), 2.41 (s, 3H), 3.79 (s, 3H), 6.72- 6.79 (m, 2H) and 6.94 (d, J= 8.4 Hz, 1H); 13C NMR (CDC13) delta11.6, 16.7, 25.5, 55.6, 111.9, 113.0, 116.2, 122.6, 131.3, 144.9, 157.1, 160.1, 165.2 and 168.1; mass spectrum (APCI), m/z calcd for C14H16C1N202 (M+H)+ 279.0895, found 279.0888.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1780-33-2, 4,6-Dichloro-2,5-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; ALAM, Mohammad Parvez; JOHN, Varghese; JOGODZINSKA, Barabara; (120 pag.)WO2018/48953; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 42754-96-1, 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.42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H2Cl2N4, molecular weight is 189, as common compound, the synthetic route is as follows.

Intermediate 70; 4,6-Dichloro-l-(tetrahvdro-2H-pyran-2-yl)-lH-pyrazolor3,4-dlpyrimidine 103496-1PTo a solution of 4,6-dichloro-lH-pyrazolo[3,4-d]pyrimidine (Intermediate 71, 2 g, 10.58 mmol) and/?-Ts-OEta (0.201 g, 1.06 mmol) in DCM (30 mL) and THF (30.0 mL), was added 3,4- dihydro-2H-pyran (1.335 g, 15.87 mmol). The resulting solution was stirred overnight at ambient temperature whereupon the volatiles were removed under reduced pressure. The residue left, was dissolved in DCM and the organic layer was washed with saturated aqueous sodium carbonate

The chemical industry reduces the impact on the environment during synthesis 42754-96-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 16075-42-6, 2-Amino-4-(trifluoromethyl)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, name: 2-Amino-4-(trifluoromethyl)pyrimidine, blongs to pyrimidines compound. name: 2-Amino-4-(trifluoromethyl)pyrimidine

To a solution of 2-amino-4-trifluoromethylpyrimidine (25 g, 0.15 mol) in CH3CN (600 mL) was added in the dark a solution of N-bromosuccinimide (34.8 g, 195 mmol) in acetonitrile (200 mL) over a period of 2.5 h. The reaction mixture was stirred for 4.5 h at RT and then concentrated. The residue was dissolved in EtOAc and H2O, the organic solvents were separated, washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography using EtOAc in hexane from 10% to 40% to provide the title compound as a beige solid (31.2 g, 85%). LC-MS: Rt 0.82 min; (LCMS method 2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16075-42-6, 2-Amino-4-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; Fairhurst, Robin Alec; Furet, Pascal; Kalthoff, Frank Stephan; Lerchner, Andreas; Rueeger, Heinrich; US2014/135330; (2014); 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. 49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine, the common compound, a new synthetic route is introduced below. Computed Properties of C5H5ClN2S

Step 1: In a sealed vial under nitrogen, 4-chloro-2-methylthiopyrimidine 18 (0.24 mL, 2.0 mmol, 2.0 eq) is added to 4-chlorophenylboronic acid (156 mg, 1 mmol, 1 .0 eq), Na2C03 (530 mg, 5 mmol, 5.0 eq) and tetrakis(triphenylphosphine) palladium (0) (57.8 mg, 0.05 mmol, 0.05 eq) in a degassed mixture of toluene (4 mL), EtOH (0.8 mL) and H20 (0.2 mL). The reaction is heated at 90C for 18 h. After cooling, the reaction is diluted with water and EtOAc and the aqueous layer is acidified by HCI 1 N to pH 3-4 before being extracted with EtOAc. The combined organic layers are dried over anhydrous Na2S04 and evaporated under reduced pressure. The residue is purified by flash chromatography (Heptane/EtOAc 50:1 ) to afford intermediate 19. LC-MS conditions: LC-MS 5.

The synthetic route of 49844-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; CIANA, Claire-Lise; SIEGRIST, Romain; WO2014/72903; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 22536-63-6 ,Some common heterocyclic compound, 22536-63-6, molecular formula is C5H5ClN2O, 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.

[Show Image] (1) Under an argon atmosphere, sodium hydride (100 mg) was added to a solution of 4-iodoaniline (220 mg) and 2-chloro-4-methoxypyrimidine (145 mg) in anhydrous DMF (10 ml), and the resulting mixture was stirred at 125C for 21 hours. The reaction solution was cooled to room temperature and water was added thereto, followed by extracting the resulting mixture with ethyl acetate. Organic layer was washed twice with water and once with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate = 10/1) to obtain N-(4-iodophenyl)-4-methoxypyrimidin-2-amine (46 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22536-63-6, its application will become more common.

Reference:
Patent; Toray Industries, Inc.; EP2033637; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 332133-92-3, 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. 332133-92-3, name is 4-(Tributylstannyl)pyrimidine. A new synthetic method of this compound is introduced below.

A mixture of 3 -(8-amino-S -bromo-2-(pyridin-2-ylmethyl)- [1 ,2,4jtriazolo [1,5 – ajpyrazin-6-yl)benzonitrile (15 mg, 0.037 mmol), 4-(tributylstannyl)pyrimidine (20mg, 0.055 mmol), and copper(I) chloride (4.4 mg, 0.044 mmol), lithium chloride (1.9 mg, 0.044 mmol) and tetrakis(triphenylphosphine)palladium(0) (4.3 mg, 3.7 imol) in THF (1 mL) was purged with N2, and stirred at 90 C for 2 h. The reaction mixture was then cooled to room temperature, diluted with methanol, and purified via prepLCMS (pH 2, acetonitrile/water with TFA) to give the desired product as a TFA salt.LC-MS calculated for C22H16N9 (M+H): mlz = 406.2; found 406.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,332133-92-3, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; HOANG, Gia; WANG, Xiaozhao; CARLSEN, Peter Niels; GAN, Pei; LI, Yong; QI, Chao; WU, Liangxing; YAO, Wenqing; YU, Zhiyong; ZHU, Wenyu; (333 pag.)WO2020/10197; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 947533-45-1, 2-bromo-5-fluoropyrimidine, 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, 947533-45-1, blongs to pyrimidines compound. COA of Formula: C4H2BrFN2

A solution of NiCl2(glyme) (0.084 g, 0.384 mmol), 4-ie/7-butyl-2-(4-ie/7-butyl-2-pyridyl)pyridine, and Ir{dF(CF3)ppy}2(dtbpy)PF6(0.086 g, 0.077 mmol) in DME (80 mL) was sparged with N2for 15 min. The nickel solution was added to a mixture of //77-butyl 3- (bromomethyl)pyrrolidine-l-carboxylate (2.03 g, 7.68 mmol), 2-bromo-5-fluoro-pyrimidine (1.70 g, 9.61 mmol), tris(trimethylsilyl) silane (2.87 g, 11.5 mmol, 3.54 mL), and lithium hydroxide (0.736 mg, 30.7 mmol). After the mixture was sparged with N2(15 min), the reaction was irradiated with blue LEDs (48 watts 450 hv) overnight at 40 C. Celite was added to the reaction, and the mixture was filtered and concentrated in vacuo. The residue was purified over Si02(0-100% EtOAc:heptane) to afford the title compound (0.760 g). LCMS (ESI): [M – i-Bu] 226. 1HNMR: (500 MHz, CDCl3) d 8.39 (br d, 7=9.46 Hz, 2 H), 3.30 – 3.46 (m, 2 H), 3.10 – 3.21 (m, 1 H), 2.85 – 2.96 (m, 3 H), 2.54 – 2.66 (m, 1 H), 1.80 – 1.91 (m, 1 H), 1.42 – 1.57 (m, 1 H), 1.27 – 1.35 (m, 9 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,947533-45-1, its application will become more common.

Reference:
Patent; BIOGEN MA INC.; GENUNG, Nathan; GUCKIAN, Kevin, M.; VESSELS, Jeffrey; ZHANG, Lei; GIANATASSIO, Ryan; LIN, Eaward Yin, Shiang; XIN, Zhili; (136 pag.)WO2019/178191; (2019); 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. 444731-75-3, name is N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine, the common compound, a new synthetic route is introduced below. Safety of N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine

To a stirred suspension of the product of Intermediate Example 4 (1.1 g, 3.8 mmol) in 14 mL of MeOH, was added 5-amino-2-methylbenzenesulfonamide (0.78 g, 4.2 mmol, 1.1 equiv) at room temperature. The reaction mixture was heated at reflux for 3 h, then 4 M HCI in 1 ,4-dioxane (19 mul_, 0.076 mmol) was added in one portion. After 4 h, the suspension was cooled to room temperature, and filtered. The resulting solid was washed with 10 mL of MeOH and dried in vacuo to yield 1.3 g (72%) of 5- ({4-[(2,3-dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl}amino)-2-methyl benzenesulfonamide monohydrochloride as a white solid. 1 H NMR (DMSO-d6, 400 MHz) delta 10.95 (s, 1 H), 8.36 (s, 1 H), 7.86 (d, J= 8.8 Hz, 2H), 7.64-7.59 (m, 2H), 7.40 (m, 3H), 6.93 (dd, J = 8.8, 2.0 Hz, 1 H), 5.92 (s, 1 H), 4.08 (s, 3H), 3.57 (s, 3H), 2.65 (s, 3H), 2.56 (s, 3H).

The synthetic route of 444731-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/64753; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 183438-24-6, 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 183438-24-6, name is 5-Bromo-2-iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a clean and dry reactor containing 20.04 g of isopropyl 2-bromo-3-cyclopentyl-1-methyl-1H-indole-6-carboxylate, 1.06 g of Pd(TFP)2Cl2 (3 mol %) and 0.76 g of tri(2-furyl)phosphine (6 mol %) was charged 8.35 g of triethylamine (1.5 equivalent), 39.38 g of CH3CN at 23±10 C. under nitrogen or argon and started agitation for 10 min 9.24 g of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane was charged into the reactor. The mixture was heated to reflux (ca. 81-83 C.) and stirred for 6 h until the reaction completed. The batch was cooled to 30±5 C. and quenched with a mixture of 0.99 g of water in 7.86 g of CH3CN. 17.24 g of 5-bromo-2-iodopyrimidine and 166.7 g of degassed aqueous potassium phosphate solution (pre-prepared from 46.70 g of K3PO4 and 120 g of H2O) was charged subsequently under argon or nitrogen. The content was heated to reflux (ca. 76-77 C.) for 2 h until the reaction completed. 4.5 g of 1-methylimidazole was charged into the reactor at 70 C. The batch was cooled to 20±3 C. over 0.5 h and hold at 20±3 C. for at least 1 h. The solid was collected by filtration. The wet cake was first rinsed with 62.8 g of 2-propanol, followed by 200 g of H2O. The solid was dried under vacuum at the temperature below 50 C. [0095] Into a dry and clean reactor was charged dried I, 10 wt % Norit SX Ultra and 5 V of THF. The content was heated at 60±5 C. for at least 1 h. After the content was cooled to 35±5 C., the carbon was filtered off and rinsed with 3 V of THF. The filtrate was charged into a clean reactor containing 1-methylimidazole (10 wt % relative to I). After removal of 5 V of THF by distillation, the content was then cooled to 31±2 C. After the agitation rate was adjusted to over 120 rpm, 2.5 V of water was charged over a period of at least 40 minutes while maintaining the content temperature at 31±2 C. After the content was agitated at 31±2 C. for additional 20 min, 9.5 V of water was charged into the reactor over a period of at least 30 minutes at 31±2 C. The batch was then cooled to about 25±3 C. and stirred for additional 30 minutes. The solid was collected and rinsed with 3 V of water. The wet product I was dried under vacuum at the temperature below 50 C. (19.5 g, 95 wt %, 76% yield).

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; Boehringer Ingelheim International GmbH; LI, Zhibin; YANG, Bing-Shiou; YIP, Kazuhiko; US2013/261134; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia