7461-50-9 | Pyrimidines

23-Sep News The origin of a common compound about 7461-50-9

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 7461-50-9, 2-Chloropyrimidin-4-amine.

Reference of 7461-50-9, 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 7461-50-9, name is 2-Chloropyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of (6-(6,6-difluoro-3-azabicyclo[3.1.0]hexan-3-yl)pyridin-3-yl)boronic acid (240.0 mg, 1.0 mmol)2-chloropyrimidin-4-amine (129.0 mg, 1.0 mmol) in 1,4-dioxane (5 mL) and H2O (1 mL) was added potassium carbonate (276.4 mg, 2.0 mmol). After the mixture was degassed with N2 for 3 times, Pd(PPh3)4 (57.8 mg, 0.05mmol) was added under N2 and the mixture was stirred at 90 oC for 3 hrs. The reaction mixture was cooled down and poured into EA. The organic phase was separated, washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography (eluted with PE : EA = 1: 1) to afford the title product (140 mg, 58.1 % yield) as a white solid. Retention time (LC-MS): 0.365 min. MH+ 290.

Reference:
Patent; HYDRA BIOSCIENCES, INC.; CHENARD, Bertand, L.; WU, Xinyuan; (351 pag.)WO2016/44792; (2016); A1;,
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18-Sep-21 News Extracurricular laboratory: Synthetic route of 7461-50-9

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7461-50-9, 2-Chloropyrimidin-4-amine, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 7461-50-9, 2-Chloropyrimidin-4-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, Formula: C4H4ClN3, blongs to pyrimidines compound. Formula: C4H4ClN3

To a glass vial was added (4-methoxyphenyl)boronic acid (0.15 g, 1.0 mmol), 2-chloropyrimidin- 4-amine (0.13 mg, 1.0 mmol), Pd(Amphos)2Cl2 (35 mg, 0.050 mmol), a 2M solution of Na2C03 (0.75 mL, 1.5 mmol) and acetonitrile (2.5 mL). The mixture was degassed by nitrogen bubbling for 20 min. The reaction vial was sealed and stirred at 110 C in an oil bath for 2 h. The reaction mixture was cooled to room temperature, filtered and concentrated. The crude product was purified by flash chromatography on silica to give the title compound (141 mg, 70%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7461-50-9, 2-Chloropyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); A1;,
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Brief introduction of 7461-50-9

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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. 7461-50-9, name is 2-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, 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 2-Chloropyrimidin-4-amine

4-Amino-2-chloropyrimindine (1.3 g, 10.03 mmol) was suspended in Ac20 (9.47 mL, 100 mmol) then heated at 140 C for 3 h. The reaction was cooled to rt then Et20 (50 mL) was added and the resulting precipitate was filtered off This solid was purified by normal phase column chromatography [CyH/(EtOAc/EtOH 3:1) 90/10 to 50/501 to afford N-(2- chloropyrimindin-4-yl)acetaminde (500 mg, 2.91 mmol, purity: 100 %, recovery: 29 %) as awhite powder. LCMS (m/z) 172 and 174 (M+H), retention time: 1.29 min LC/MS Method1.

With the rapid development of chemical substances, we look forward to future research findings about 7461-50-9.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DAUGAN, Alain Claude-Marie; DONCHE, Frederic G.; FAUCHER, Nicolas Eric; GEORGE, Nicolas S.; (243 pag.)WO2018/92089; (2018); A1;,
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Sources of common compounds: 2-Chloropyrimidin-4-amine

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. 7461-50-9, 2-Chloropyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference of 7461-50-9, Adding some certain compound to certain chemical reactions, such as: 7461-50-9, name is 2-Chloropyrimidin-4-amine,molecular formula is C4H4ClN3, 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 7461-50-9.

A microwave reaction vessel was charged with 4-amino-2-chloropyrimidine (100 mg, 0.774 mmol, 1.0 eq), 2-methanesulfonyl-2-methylpropan-l -ol (353 mg, 2.33 mmol, 3.0 eq), and potassium carbonate (160.3 mg, 1.16 mmol, 1.5 eq) in propan-2-ol (1 mL). The reaction was stirred at room temperature for 1 min and heated under microwave irradiation at 200 C for 2.5 h (Biotage Initiator, maximum pressure set at 22 bar). The reaction mixture was cooled to room temperature and purified by chromatography on silica (solvent gradient: 0-10% 2M methanolic ammonia in ethyl acetate) to afford the title compound (163 mg, 86%). LCMS (ESI): [M+H]+ 246.3.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; DIEDERICH, Francois; DOTSON, Jennafer; HANAN, Emily; HEFFRON, Timothy; LAINCHBURY, Michael; HEALD, Robert; SEWARD, Eileen M.; WO2014/210354; (2014); A1;,
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Analyzing the synthesis route of 7461-50-9

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7461-50-9, 2-Chloropyrimidin-4-amine, and friends who are interested can also refer to it.

Related Products of 7461-50-9, 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. 7461-50-9, name is 2-Chloropyrimidin-4-amine. A new synthetic method of this compound is introduced below.

To a reaction vessel was added 2-chloropyrimidin-4-amine (1.0 g, 8.0 mmol, 1.1 equiv), 3,3- dimethylpiperidin-4-ol (1.0 g, 9.0 mmol, 1.0 equiv), triethylamine (3.0 g, 30 mmol, 4.0 equiv), and 2-propanol (5 mL). The sealed reaction vessel was heated under microwave irradiation at 150 C for 45 min. The reaction mixture was cooled to room temperature, diluted with saturated aqueous sodium bicarbonate and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to afford l-(4-aminopyrimidin-2-yl)-3,3- dimethyl-piperdin-4-ol (1.24 g, 70%). LCMS (ESI): [M+H]+ = 223.2; lH NMR (300 MHz, DMSO-d6) delta 7.69 (d, J= 5.6 Hz, 1H), 6.28 (s, 2H), 5.64 (d, J= 5.6 Hz, 1H), 4.55 (d, J= 4.7 Hz, 1H), 4.33 – 4.22 (m, 1H), 4.02 (dd, J= 12.8, 1.7 Hz, 1H), 3.25 (dd, J= 9.4, 4.6 Hz, 1H), 3.08 – 2.96 (m, 1H), 2.75 (d, J= 13.0 Hz, 1H), 1.66 – 1.54 (m, 1H), 1.47 – 1.35 (m, 1H), 0.87 (s, 3H), 0.74 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7461-50-9, 2-Chloropyrimidin-4-amine, and friends who are interested can also refer to it.

Introduction of a new synthetic route about 7461-50-9

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, 7461-50-9, 2-Chloropyrimidin-4-amine.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 7461-50-9, name is 2-Chloropyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

2-Chloropyrimidin-4-ylamine (3.5 g, 27.0 mmol), 4-methoxypiperidine hydrochloride (4.09 g, 27.0 mmol) and Cs2C03 (26.4 g, 81.0 mmol) were suspended in DMF (60 mL) and heated at 120 C for 18 h. The reaction mixture was partitioned between water and EtOAc. The aqueous phase was washed with EtOAc (x 2) and the combined organic phases were washed with brine, dried (MgSO i), and concentrated in vacuo affording the title compound as a solid (2.5 g). The aqueous phase was concentrated in vacuo and the slurry was extracted with EtOAc. The volatiles were removed in vacuo and the resulting residue was purified by chromatography (Si-PCC, gradient 0- 100% EtOAc in cyclohexane) and then triturated with cyclohexane affording a second batch of the title compound (2.38 g, 87% combining the two batches). lH NMR (400 MHz, CDC13) delta: 7.94 (1H, d, J=5.60 Hz), 5.74 (1H, d, J=5.60 Hz), 4.53 (2H s), 4.33-4.24 (2H, m), 3.47-3.37 (4H, m), 3.33-3.24 (2H, m), 1.98-1.87 (2H, m), 1.60-1.47 (2H, m).

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, 7461-50-9, 2-Chloropyrimidin-4-amine.

New learning discoveries about 7461-50-9

With the rapid development of chemical substances, we look forward to future research findings about 7461-50-9.

In a reaction apparatus with a reflux condenser, 2,3-dimethyl-6-chloro-2H-carbazole 18gAnd 14.5 g of 2-chloro-4-amino-pyrimidine were added to 220 mL of N,N-dimethylformamide.In an ice salt bath at 0 C under nitrogen protection,50 mL of a tetrahydrofuran solution containing 12% of sodium hydride in a content of 60% was slowly added dropwise.After the addition was completed, the temperature was raised to room temperature, and the reaction was continued for 5 hours.Then use the existing strong alkaline environment of the reaction system,100 mL of tetrahydrofuran solution in which 14 g of methyl iodide was dissolved was added dropwise.The reaction was continued for 6 h at room temperature, and new substances appeared in the reaction system monitored by TLC.And the content of the new substance in the reaction system is determined by HPLC to occupy 90% to 95%,The reaction system was cooled to 10 C, and then dilute hydrochloric acid was slowly added dropwise.The pH of the reaction solution was adjusted to be neutral, and then tetrahydrofuran was removed by evaporation under vacuum.The reaction solution was allowed to stand for a while, and then 70 mL of a saturated ammonium chloride solution was added to the reaction solution.Then, 250 mL of chloroform was added to the reaction solution.After stirring for 10 min, the organic phase was separated and the organic phase was concentrated.The concentrate is recrystallized from acetone and cyclohexane to giveN-(2-chloropyrimidin-4-yl)-N-methyl-2,3-dimethyl-2H-indazole-6-amine 20.7 g;

With the rapid development of chemical substances, we look forward to future research findings about 7461-50-9.

Reference:
Patent; Jinan Ai Si Pharmaceutical Technology Co., Ltd.; Peng Lizeng; Mao Longfei; Liu Xiaofei; Yao Xiaojun; Liu Huanxiang; Bai Qifeng; Liang Lixian; (17 pag.)CN110028495; (2019); A;,
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Application of 2-Chloropyrimidin-4-amine

Synthetic Route of 7461-50-9 ,Some common heterocyclic compound, 7461-50-9, molecular formula is C4H4ClN3, 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.

Example 1 N-(4-((4-Aminopyrimidin-2-yloxy)methyl)benzyl)-2,2,2-trifluoroacetamide (1) 760 mg (3.25 mmol) 2,2,2-Trifluoro-N-(4-hydroxymethyl-benzyl)-acetamide is dissolved in 3 mL dry dimethylacetamide under argon atmosphere, and 273 mg (8.15 mmol) NaH is added over 5 min. 211 mg (1.63 mmol) 2-Chloropyrimidin-4-amine is then added and the solution stirred at 90C over night. 1 mL Water is added carefully to quench all excess NaH, and the mixture poured into 50 ml of 0.5 N HCI. The crude product is extracted with ethyl acetate, the combined organic phases washed with brine and dried over MgSO4. After evaporation of the solvent, the product is purified by flash column chromatography (gradient ethyl acetate:cyclohexane from 1:1 to 3:1). Yield: 350 mg (52%). ESI-MS m/z 327 [M+H]+.

Reference:
Patent; EPFL Ecole Polytechnique Federale de Lausanne; EP1882688; (2008); A1;,
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Extracurricular laboratory: Synthetic route of 2-Chloropyrimidin-4-amine

With the rapid development of chemical substances, we look forward to future research findings about 7461-50-9.

To a solution of sodium hydride (0.817 g, 34.1 mmol) in Tetrahydrofuran (THF) (30 mL) at room temperature was added a solution of (R)-(2,2-dimethyl-l,3-dioxolan-4- yl)methanol (3 g, 22.70 mmol) in THF (5 mL) over 1 min and stirred at room temperature for 15 min then add 2-chloropyrimidin-4-amine (2.059 g, 15.89 mmol) portion wise at room temperature. The reaction mixture was stirred at 65 C for 16h. The reaction mixture was poured in to water and extracted with EtOAc (3 X lOOmL). Then the combined organic layer was washed with water, brine solution, dried over sodium sulfate and evaporated to get 4.0 g of crude compound. The crude compound was purified by column chromatography using 100-200 silica gel mesh and eluted with 2-3% MeOH/DCM to get pure compound (2.5g, 10.42 mmol, 46%), LCMS (m/z) 226.2 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 7461-50-9.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
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Some tips on Related Products of 7461-50-9

Related Products of 7461-50-9, 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 7461-50-9, name is 2-Chloropyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-(5-aminopyrazin-2-yl)-6-cyclobutyl-2-fluorophenol (17.0 g, 65.6 mmol), K2CO3 (13.6 g, 98.4 mmol), 2-chloropyrimidin-4-amine (8.9 g, 69 mmol), 18-crown-6 (0.87 g, 3.3 mmol), and DMA (131 mL) was stirred at 120 Celsius for 15 hours. Water (306 mL) was added, and the reaction mixture cooled to room temperature. Solid precipitate was collected by vacuum filtration and dried in a vacuum oven at 70 Celsius to give the crude product (23.1 g, 100%). The solid was recrystallized from EtOH and treated successively with activated charcoal and silica-supported thiol to remove residual Pd and afford the title compound (13.0 g, 56%). MS (ESI): mass calcd. for C18H17FN6O, 352.14; m/z found, 353.2 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 8.25 (s, 1H), 8.01 (d, J=1.5, 1H), 7.83 (d, J=5.8, 1H), 7.66 (m 1H), 7.23 (d, J=8.3, 1H), 7.06 (s, 2H), 6.67 (s, 2H), 6.17 (d, J=5.8, 1H), 3.60-3.47 (m, 1H), 2.19-2.01 (m, 4H), 1.98-1.85 (m, 1H), 1.80-1.68 (m, 1H).

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2015/252008; (2015); A1;,
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