Category: pyrimidines

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

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

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

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

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

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

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: 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

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

Application of 5750-76-5, 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. 5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, 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.

After adding a solvent N-methylpyrrolidone 12L to a 20 L double-layer glass reactor, the mechanical stirrer was turned on to stir.Then the substrate 2-(isopropylsulfonyl)aniline (199.3 g, 1 mol) was added sequentially.Potassium tert-butoxide (168.3 g, 1.5 mol),2,4,5-trichloropyrimidine (238.5 g, 1.3 mol),Zinc acetate (55.0 g, 0.3 mol),After stirring and dispersing uniformly, the temperature is raised to 120±2 C. for the heat preservation reaction;After 10 h, the reaction solution was taken for HPLC analysis (area normalization method: substrate 2-(isopropylsulfonyl)aniline was 1.18%, product 98.72%,The remaining amount is unknown impurity),The reaction was continued for 2 hours, and the reaction solution was subjected to HPLC analysis (area normalization method: substrate 2-(isopropylsulfonyl)aniline was 0.14%,99.52% of the product, the balance is unknown impurities);[0055] Stop the reaction, cool to 20-30 C and transfer to a 50L reactor;Add 8 L of isopropyl acetate under stirring, then add 30% V acetic acid aqueous solution to adjust the pH of the system to 7.5-7.8, stir 10-20pieta; – add 5.0L of purified water, stir for 8-lOmin, then let stand for 20-30 min. The liquid layer was collected, and the upper layer of isopropyl acetate was collected. The lower aqueous phase was extracted twice with isopropyl acetate, and 6.0 L of isopropyl acetate layer was added each time; all the isopropyl acetate layers were combined and washed with 10 L of saturated brine. After standing for liquid separation, the isopropyl acetate layer was collected, and then heated to 40-45 C, and 12 L of n-heptane was added dropwise with stirring, and a white solid precipitated in the system during the dropwise addition.After the addition, the temperature is lowered to 10-20 C.Then, the temperature is raised to 50-60 C, the temperature is kept 10-20pieta, and then naturally cooled to room temperature, filtered, and the filter cake is collected and dried under reduced pressure at 40-45 C to obtain 318.1 g of an off-white solid, the yield is 92.1%;The purity of 2,5-dichloro-N-[2-(isopropylsulfonyl)phenyl]pyrimidin-4-amine in white solid was 99.88%, and the unreacted substrate 2-(isopropylsulfonate) was detected by HPLC. Acyl) aniline 0.04%, the balance is unknown impurities

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 5750-76-5, 2,4,5-Trichloropyrimidine.

Reference:
Patent; Liu Gengxi; Chen Lanhua; Ji Hui; Li Jing; Liang Li; (8 pag.)CN109020898; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia