Tag: M.W:200-300

Synthetic Route of 13162-26-0, 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. 13162-26-0, name is 2,4-Dichloro-6-methyl-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

Step A: 4-(4-bromo-2,6-dimethylphenoxy)-2-chloro-6-methyl-5-nitropyrimidine; A solution of LiHMDS in THF (1M, 77 ml, 77 mmol) was added at -78 C. to a mixture of 2,6-dimethoxy-4-bromophenol (14.07 g, 70 mmol) in THF (100 ml) over 15 minutes. The mixture was stirred for an additional 2 hours. Phenoxide salt was observed as solid suspension. The mixture was cooled with liquid nitrogen to a temperature around -100 C. and then a solution of 2,6-dichloro-4-methyl-5-nitropyrimidine (17.47 g, 84 mmol) in THF (50 ml) was added rapidly to the mixture, which turned dark red. The reaction was kept at a temperature around -100 C. for 1 hour. After warming to room temperature, the mixture was filtered and the solid was washed with ethanol to yield 16.75 g of the title product. The filtrate was concentrated and crystallized to obtain an additional 5.60 giving a total amount of 22.35 g of desired compound (60 mmol, 85%). 1H NMR (CDCl3, 400 MHz) delta 2.11 (s, 6H), 2.63 (s, 3H), 7.27 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13162-26-0, 2,4-Dichloro-6-methyl-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Ardea Biosciences; US2009/162319; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1060816-58-1, Adding some certain compound to certain chemical reactions, such as: 1060816-58-1, name is 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H3BrClN3, 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 1060816-58-1.

To a stirred solution of 5-bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine (3.0 g, 12.9 mmol), cyclohexanol (2.59 g, 25.9 mmol) and PPh3 (8.46 g, 32.3 mmol) in THF (100 mL) was added DEAD (5.62 g, 32.3 mmol) dropwise at 0 C. The resulting solution was stirred for 16 h at room temperature under nitrogen atmosphere. The resulting solution was condensed under reduced pressure. The residue was purified by reversed phase flash chromatography with the following conditions: Column: WelFlash TM C18-I, 20-40 um, 330 g; Eluent A: Water (plus 10 mmol/L TEA); Eluent B: ACN; Gradient: 70% – 90% B in 25 min; Flow rate: 80 mL/min; Detector: UV 200/220 nm; desired fractions were collected at 78% B and concentrated under reduced pressure to afford 5-bromo-2-chloro-7-cyclohexyl-7H-pyrrolo[2,3-d]pyrimidine (1.7 g, 42%) as a white solid.1H NMR (400 MHz, DMSO-d6) d 8.84 (s, 1H), 8.11 (s, 1H), 4.67-4.49 (m, 1H), 1.96-1.64 (m, 7H), 1.47 (q, J = 13.5 Hz, 2H), 1.32-1.12 (m, 1H). LC/MS (ESI, m/z): [(M + 1)]+ = 313.95, 315.95

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. 1060816-58-1, 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; JI, Nan; MAINOLFI, Nello; WEISS, Matthew; (977 pag.)WO2020/10210; (2020); 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.51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, molecular formula is C7H6Cl2N2O2, molecular weight is 221.0407, as common compound, the synthetic route is as follows.Computed Properties of C7H6Cl2N2O2

Ethyl 2-chloro-4-(4-chloro-3-methoxyphenylamino)pyrimidine-5-carboxylate (RJ1- 061): A mixture of ethyl 2,4-dichloropyrimidine-5-carboxylate (0.442 g, 2.0 mmol), 4-chloro-3- methoxyaniline (0.331 g, 2.1 mmol), DIPEA (0.42 mL, 2.4 mmol), and iPrOH (2 mL) was added to a 5 mL microwave vial which was then sealed and placed in a hot oil bath with stirring at 85 C overnight for 17 hours. At this point, a brown solid had formed and this was then washed with iPrOH (10 mL), water (10 mL), iPrOH (10 mL), and hexanes (10 mL) to yield RJ1-061 as a brown solid (0.570 g, 83%). m.p. = 119 C (decomposed). XH NMR (400 MHz, DMSO-) delta 10.27 (s, 1H), 8.81 (s, 1H), 7.48 (d, J= 2.3 Hz, 1H), 7.43 (d, J= 8.6 Hz, 1H), 7.28 (dd, J= 8.6, 2.3 Hz, 1H), 4.37 (q, J= 7.1 Hz, 2H), 3.85 (s, 3H), 1.34 (t, J= 7.1 Hz, 3H). LRMS (ESI+) m/z 342.1 (MC135C135+H)+, 344.0 (MC135C137+H)+, 346.0 (MC137C137+H)+; (ESI-) m/z 339.3 (MC135C135-H)-; HRMS (ESI+) m/z calculated for C14H13CI2N3O3 (M+H)+ 342.04067, found 342.04100.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,51940-64-8, Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); 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 59549-51-8, name is 5-Bromo-2-chloro-4-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H4BrClN2S

To5-bromo-2-chloro-4-(methylthio)pyrimidine (3 g, 12.53 mmol) in dioxane (12.53 mL) was added 2-methylpropan-2-amine (7.93 mL, 75 mmol). The mixture was stirred at 100 C overnight in a sealed vessel. The solvent was removed under reduced pressure and the residue was dissolved in 100 mL ethyl acetate and washed with 50 mL of a 1M aqueous solution of sodium hydrogen phosphate. The aqueous layer was back-extracted with 50 mL ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to give 5-bromo-N-tert-butyl-4-(methylthio)pyrimidin-2- amine (3.4 g, 12.31 mmol, 98% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.61 – 8.72 (m, 1 H), 8.08 (s, 1 H), 6.95 – 7.17 (m, 1 H), 2.48 (s, 2 H), 1.38 (s, 9 H).MS (ESI) m/z 276.0 [M+l]+ and 278.2 [M+l]+.

With the rapid development of chemical substances, we look forward to future research findings about 59549-51-8.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 784150-41-0 ,Some common heterocyclic compound, 784150-41-0, molecular formula is C6H3BrClN3, 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.

4-(1,1-Dioxothiomorpholinyl)phenyl)boronic acid pinacol ester (1.1 g, 3.3 mmol) was added to a 100mL of flask and added with 6-bromo-4-chloro-7-((2-(trimethylsilyl) ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (440 mg 1.90 mmol), potassium carbonate (0.53 g, 3.8 mmol), dioxane (40 mL), Pd (dppf) Cl2(139 mg, 0.18 mmol), and water (4 mL) successively. The reaction mixture was stirred at 80C for 16 h under argon atmosphere. The reaction mixture was cooled to rt. and concentrated under reduced pressure to dryness. The residues were purified by column chromatography (eluent: PE:EtOAc, 3:1) to give 100 mg of the title compound as pale yellow solid (yield of 14.5%).

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. 784150-41-0, 6-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The National Institutes Of Pharmaceutical Research; YIN, Huijun; YAN, Xu; ZONG, Libin; TIAN, Weixue; ZHENG, Li; DOU, Haoshuai; YANG, Yan; (68 pag.)EP3556761; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1211443-61-6 ,Some common heterocyclic compound, 1211443-61-6, molecular formula is C14H17ClN4O, 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.

A solution of 3-(3-aminophenyl)-5-mo holino-7H-thieno[3,2-b]pyran-7-one from step 1 (0.050 g, 0.152 mmol), 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6- carboxamide (0.055 g, 0.182 mmol), BINAP (0.017 g, 0.029 mmol), and cesium carbonate (0.151 g, 0.458 mmol) in 1,4-doxane (2.0 mL) was degassed under a flow of argon for 15 min. Pd(OAc)2 (0.010 g, 0.025 mmol) was added to the mixture and degassed for 10 min. Then, the reaction mixture was heated to 95-100 C for 12 h. The reaction mixture was next cooled to the ambient temperature and concentrated under reduced pressure. The crude product was purified by flash column chromatography (silica-gel), eluting with DCM/MeOH (97:3) gradient. The fractions containing the product were concentrated to yield 28% of compound 17 (0.024 g, 0.041 mmol). Physical state: Pale yellow solid. R = 0.30 (mobile phase: 5% MeOH/DCM) on silica gel plate. Proton NMR and mass spectra are consistent with the structure of product. Calculated molecular weight: 584.2 Dalton. MS (ESI) m/z = 585.42 [M + H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1211443-61-6, its application will become more common.

Reference:
Patent; SIGNALRX PHARMACEUTICALS, INC.; MORALES, Guilermo, A.; GARLICH, Joseph, R.; DURDEN, Donald, L.; (166 pag.)WO2018/140730; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 51940-64-8, 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 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Dichloropyrimidine 1.4 (3.39 g, 15 mmol) was diluted with toluene (8 mL) and treated with benzyltriethylammonium chloride (0.68 g, 3 mmol) then sodium thiomethoxide (1.2 g, 17 mmol). The resulting suspension was then diluted with 8 mL of water and stirred vigorously for one hr at which time the starting material was found to be consumed by UPLC. The mixture was then diluted with water and ethyl acetate and the layers separated. The organic phase was extracted once with ethyl acetate and the combined organic layers concentrated in vacuo. The resulting solid was then triturated with ca. 15 mL of diethyl ether and the solid isolated by filtration and washed with a small amount of diethyl ether resulting in a light beige solid (0.66 g, 19%). MS found for C8H9ClN2O2S as (M+H)+ 233.0, 235.1.

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 51940-64-8, Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; BAUER, Shawn M.; ROSE, Jack W.; SONG, Yonghong; XU, Qing; MEHROTRA, Mukund; HUANG, Wolin; PANDEY, Anjali; WO2010/129802; (2010); A1;,
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. 69696-35-1, name is 5-Bromo-4-chloro-2,6-dimethylpyrimidine. A new synthetic method of this compound is introduced below., COA of Formula: C6H6BrClN2

c) 5-bromo-2,4-dimethylpyrimidine. A mixture of 5-bromo-4-chloro-2,6- dimethylpyrimidine (2.73 g, 12.33 mmol), 4-methylbenzenesulfonohydrazide (4.19 mL, 37.0 mmol) and chloroform (40 mL) was heated at 90 C for 16 hours. The solution was cooled and the solid filtered and washed with chloroform. LCMS revealed this solid (4.75g) was the desired intermediate. A mixture of this solid and 0.94M aqueous sodium carbonate (40 mL, 37.7 mmol) was heated at 90 C for 1 .5 hours. The cooled solution was extracted with ethyl acetate 3 times, and the combined organics were washed with brine, dried (Na2S04) and concentrated to afford the title compound (1 .17 g, 51 %) as a tan oil, which crystallized upon standing. LCMS (ES+) m/e 187 [M+H]+.

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, 69696-35-1, 5-Bromo-4-chloro-2,6-dimethylpyrimidine.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROWN, Kristin, K.; CHAI, Deping; DODSON, Christopher, S.; DUFFY, Kevin, J.; SHAW, Antony, Nicholas; WO2013/96151; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 38696-21-8, 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. 38696-21-8, name is 5-Bromo-N,N-dimethylpyrimidin-2-amine, molecular formula is C6H8BrN3, 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.

A mixture of 5-bromo-N,N-dimethylpyrimidin-2-amine (0.966 g, 4.78 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.46 g, 5.74 mmol), PdCl2dppf(DCM) (0.114 g, 0.14 mmol) and KOAc (1.407 g, 14.34 mmol) were placed under Ar in a 20 mL microwave flask. Anhydrous 1,2-dimethoxyethane (16 mL) was added and the flask was irradiated at 150 oC for 15 minutes. The reaction was filtered through celite, concentrated and slurried in EtOAc. The reaction was filtered through celite again and the organics were concentrated and purified by column chromatography 0 to 30 % EtOAC in Hexanes. The material was isolated as a light teal solid (0.718 g, 60 % yield). 1H NMR (400 MHz, CDCl3) delta 8.59 (s, 2H), 3.21 (s, 6H), 1.31 (s, 12H).13C NMR (100 MHz, CDCl3) delta 164.1, 83.7, 77.4, 37.2, 25.2, 24.9. HRMS (EI+) m/z calculated for C12H12BN3O2 [M+H]+: 250.1721, found: 250.17189.

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 38696-21-8, 5-Bromo-N,N-dimethylpyrimidin-2-amine.

Reference:
Patent; EMORY UNIVERSITY; SHI, Qi; KAISER, Thomas; DIRADDO, John; SNYDER, James P.; LIOTTA, Dennis C.; DENTMON, Zackery; (67 pag.)WO2017/197151; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1208901-69-2, Adding some certain compound to certain chemical reactions, such as: 1208901-69-2, name is 2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride,molecular formula is C7H8Cl3N3, 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 1208901-69-2.

2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride (20.0 g, 83.2 mmol) prepared according to Reference Example 1 was dissolved in acetonitrile (200 mL), and the solution was mixed with dimethylaminopyridine (752 mg), di-tert-butyl dicarbonate (20.9 g) and triethylamine (11.6 mL), followed by stirring at room temperature for sixteen hours. After checking the completion of the reaction by thin layer chromatography, the reaction mixture was concentrated, and the residue was dissolved in ethyl acetate. The solution was sequentially washed with a 5% aqueous citric acid solution, water, a saturated aqueous sodium bicarbonate solution and brine, was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) and thereby yielded tert-butyl 2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-6-car boxylate (22.2 g, in a yield of 88%).

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. 1208901-69-2, 2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1552842; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia