09/9/2021 News Simple exploration of 20265-38-7

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20265-38-7, 2-Methoxypyridin-3-amine, and friends who are interested can also refer to it.

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.20265-38-7, name is 2-Methoxypyridin-3-amine, molecular formula is C6H8N2O, molecular weight is 124.14, as common compound, the synthetic route is as follows.Quality Control of 2-Methoxypyridin-3-amine

Step 1-Synthesis of 6-chloro-N-(2-methoxypyridin-3-yl)pyrimidin-4-amineTo a solution of 4,6-dichloropyrimidine (660.04 mg, 4.43 mmol) in 1-butanol (10 mL) was added DIPEA (0.67 ml, 4.03 mmol) followed by 2-methoxypyridin-3-amine (500 mg, 4.03 mmol).The reaction mixture was then heated to 90° C. for 2 hr.The reaction mixture was then concentrated in vacuo and partitioned between DCM and water.A precipitate was removed by filtration and the organics extracted (2*20 ml DCM).The combined organic extracts were then washed with 0.5M HCl (5 ml) and then dried (Na2SO4), filtered and concentrated in vacuo to give the title intermediate (300 mg, LC-MS purity=83percent); LC-MS: m/z=+236.95/238.90 (M+H)+.

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Reference:
Patent; Genentech, Inc.; US2012/214762; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Analyzing the synthesis route of 20265-38-7

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 20265-38-7, 2-Methoxypyridin-3-amine.

Reference of 20265-38-7, 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 20265-38-7, name is 2-Methoxypyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: An oven-dried resealable Schlenk tube was charged with (S)-2-chloro-N-(1-(5-fluoropyridin-2-yl)ethyl)pyrimidin-4-amine (Preparation 1a, 43 mg, 0.17 mmol), 2-methoxypyridin-3-amine (23 mg, 0.19 mmol), cesium carbonate (111 mg, 0.34 mmol) and 1,4-dioxane (3 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon then tris(dibenzylideneacetone)dipalladium(0) (16 mg, 0.02 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (10 mg, 0.02 mmol) were added. After three further cycles of evacuation-backfilling with argon, the Schlenk tube was capped and then stirred and heated to 100 ºC. After 24 hours the mixture was cooled and the solvent was evaporated under reduced pressure. Ethyl acetate was added and the organic solution was washed with water (x3) and brine, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by reverse phase chromatography (C-18 silica from Waters©, water/acetonitrile/methanol as eluents [0.1percent v/v formic acid buffered] 0percent to 100percent) to yield the title compound (11 mg, 19percent) as a solid.LRMS (m/z): 341 (M+1)+.

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Reference:
Patent; Almirall, S.A.; Eastwood, Paul Robert; Bach Tana, Jordi; Pages Santacana, Lluis Miquel; EP2554544; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some tips on 2-Methoxypyridin-3-amine

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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. 20265-38-7, name is 2-Methoxypyridin-3-amine. A new synthetic method of this compound is introduced below., Product Details of 20265-38-7

(2) A solution of 2-methoxypyridin-3-amine (39.4 g) in N,N-dimethylformamide (200 mL) was cooled to -30 C., and a solution of N-bromosuccinimide (62.1 g) in N,N-dimethylformamide (100 mL) was added dropwise. After stirring for 30 minutes, the reaction solution was poured into water and extracted with chloroform. The organic layer was sequentially washed with a saturated sodium sulfite solution, water and brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1?4:1) to give 6-bromo-2-methoxypyridin-3-amine as a yellow powder (51.9 g, 80%). 1H NMR (300 MHz, CDCl3) delta ppm 3.64-3.84 (m, 2H), 3.98 (s, 3H), 6.78 (dd, J=7.9, 1.0 Hz, 1H), 6.87 (d, J=7.9 Hz, 1H). MS(+): 203 [M+H]+.

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Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD.; US2011/237791; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Extracurricular laboratory: Synthetic route of 2-Methoxypyridin-3-amine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20265-38-7, 2-Methoxypyridin-3-amine, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 20265-38-7, 2-Methoxypyridin-3-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: C6H8N2O, blongs to pyridine-derivatives compound. Formula: C6H8N2O

26.5 g (58.6 mmol) of compound IV was dissolved in 79 ml of 1,4-dioxane.To this solution was added 11.35 g (87.90 mmol)8.724 g (70.32 mmol) of diisopropylethylamine and 2-methoxy-3-aminopyridine.After refluxing for 18 hours, the residual 1,4-dioxane was removed under reduced pressure.The residual solid was dispersed in 57 ml of 95percent ethanol and stirred by suction.The filter cake was washed with 114 ml of absolute ethanol and dried.Get a yellow solid27.6g,The yield was 84.7percent.

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Reference:
Patent; Beijing Concorde Pharmaceutical Er Factory; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Zhang Dongfeng; Huang Haihong; Li Chun; Yin Dali; Lin Ziyun; Ma Chen; Wang Mijuan; Zhang Meng; Lan Pei; Zhao Limin; (11 pag.)CN109748903; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some scientific research about 2-Methoxypyridin-3-amine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20265-38-7, 2-Methoxypyridin-3-amine, and friends who are interested can also refer to it.

Application of 20265-38-7, 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. 20265-38-7, name is 2-Methoxypyridin-3-amine. A new synthetic method of this compound is introduced below.

A) Preparation of 3-(tert-Butoxycarbonylamino)-2-methoxypyridine STR12 To a stirred solution of 2.48 g (20 mmol) of 3-amino-2-methoxypyridine and 4.37 g (20 mmol) of di-tert-butyldicarbonate (Boc2 O) in 10 mL of THF was added at 0 C. 40 mL of a 1M solution of NaHMDS in THF. The mixture was then stirred at room temperature for 2 hours. The THF was removed by rotary evaporation and the residue was dissolved in EtOAc and washed twice with an equal volume of 0.1N HCl. The EtOAc layer was dried (MgSO4) and concentrated to give 3.9 g (87%) of the desired material as an oil after purification further by flash chromatography on silica gel using 95:5 hexane:EtOAc as the eluant.

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Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US5532358; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem