Tag: M.W:100-200

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.1126-44-9, name is 2-Methylsulfanylpyrimidine-4-carboxylic acid, molecular formula is C6H6N2O2S, molecular weight is 170.189, as common compound, the synthetic route is as follows.Safety of 2-Methylsulfanylpyrimidine-4-carboxylic acid

The starting material 2-methylsulfanyl-pyrimidine-4-carboxylic acid methoxy-methyl-amide can be prepared as follows. Preparation of 2-methylsulfanyl-pyrimidine-4-carboxylic acid methoxy-methyl-amide: To a slurry of 2-methylsulfanyl-pyrimidine-4-carboxylic acid (10.0 g, 59.2 mmol) in CH3CN (300 mL) is added in sequence: I-hydroxybenzotriazole hydrate (9.59 g, 71.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (13.6 g, 71.0 mmol), N,O-dimethylhydroxylamine hydrochloride (8.66 g, 88.8 mmol), and triethylamine (Et3N) (24.9 mL, 178 mmol). The resulting slurry is stirred overnight at ambient temperature. After 16 hours, the reaction mixture is poured into a saturated aqueous solution of sodium bicarbonate (300 mL) and the layers separated. The aqueous layer is extracted with ethyl acetate (3×250 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo and the resulting residue is purified over silica (100% EtOAc) to afford 10.1 g (89% yield) of the desired product as a yellow oil. 1H NMR (300 MHz, CDCl3) delta 8.65 (d, J=4.9 Hz, 1H), 7.15 (br s, 1H), 3.77 (br s, 3H), 3.38 (br s, 3H), 2.61 (s, 3H); MS (ESI) m/z 214 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1126-44-9, 2-Methylsulfanylpyrimidine-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; The Procter & Gamble Company; US2005/113392; (2005); 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. 43088-67-1, name is 4-Chloro-5-methylthieno[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 43088-67-1

Production Example 190. 4-(2-indanylamino)-5-methylthieno[2,3-d]pyrimidine 4-chloro-5-methylthieno[2,3-d]pyrimidine (92 mg, 0.50 mmol) (see J. Pharm. Soc. JAPAN, 109, 464 (1989)) and 2-aminoindan (330 mg, 2.5 mmol) in dry ethanol (1 ml) were heated to reflux under an argon atmosphere for 40 minutes. The solvent was distilled off under reduced pressure and the residue obtained was purified by silica gel chromatography (hexane: ethyl acetate = 5: 1) toobtain the title compound (140 mg, 0.50 mmol) having the following physical properties: 1H NMR (400 MHz, CDCl3): delta 2.47 (3H, s), 2.94 (2H, m), 3.50 (2H, m), 5.11 (1H, m), 5.65 (1H, br.), 6.80 (1H, s), 7.19-7.27 (4H, m), 8.47 (1H, s). MS (FAB): m/z 282 (M+H)+.

The synthetic route of 43088-67-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNTORY LIMITED; EP1132093; (2001); A1;,
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Synthetic Route of 923282-39-7 ,Some common heterocyclic compound, 923282-39-7, molecular formula is C6H5ClN4, 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.

Compound 13.1 (100 mg, 0.59 mmol, 1.00 eq.) was dissolved in 5 mL of CH3CN. Then Na2C03 (190 mg, 1.79 mmol, 3.00 eq.) and compound 1.2 (229 mg, 0.89 mmol, 1.50 eq.) were added. The reaction was stirred overnight at 80 C in an oil bath. The resulting mixture was concentrated in vacuo, diluted with 10 mL of H20 and extracted with 3×20 mL of EtOAc. Organic layers were combined and concentrated in vacuo. The crude product was purified by preparative HPLC to furnish 150 mg (80%) of I-13 as a white solid. LC-MS (ESI, m/z): [M+H]+ = 317; 1H- NMR (400 MHz, MeOD): delta 8.23 (s, 1H), 7.88 (s, 1H), 4.86 (s, 1H), 4.20-4.35 (m, 8H), 3.73-3.75 (d, 3H), 3.33 (s, 1H), 2.64-2.66 (d, 3H), 2.32-2.38 (m, 4H), 2.21-2.24 (s, 2H), 1.95-2.11 (m, 4H), 1.44-1.61 (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,923282-39-7, its application will become more common.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; BOYCE, Sarah; (135 pag.)WO2017/4133; (2017); A1;,
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Electric Literature of 17180-94-8, 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 17180-94-8, name is 5-Chloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis 193-(5-Chloro-pyrimidin-4-yl)-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl estern-Butyl lithium (2.5 , 1.2 mL, 3.00 mmol) was added dropwise to a solution of diisopropylamine (0.406 mL, 3.0 mmol) in THF (5 mL) at 0C under nitrogen and stirred for 30 minutes. The mixture was then added to a solution of 3-oxo-8-aza- bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.675 g, 3.0 mmol) and 5- chloropyrimidine (0.343 g, 3.0 mmol) in THF (1.5 mL) and stirred at 0C for 1 hour. Water and ethyl acetate were added, the organics separated, dried over sodium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 20-30% ethyl acetate/cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.14 g). LCMS m/z 340.3 [M+H]+. R.T. = 3.70 min (Analytical Method 3).

According to the analysis of related databases, 17180-94-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF EDINBURGH; WEBSTER, Scott, Peter; SECKL, Jonathan, Robert; WALKER, Brian, Robert; WARD, Peter; PALLIN, Thomas, David; DYKE, Hazel, Joan; PERRIOR, Trevor, Robert; WO2011/135276; (2011); A1;,
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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. 15598-33-1, name is 4,6-Dichloro-5-fluoropyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C4H2Cl2FN3

C. Preparation of 5-Fluoro-6-chloro-2,4-pyrimidinediamine (5) 5-Fluoro-4,6-dichloro-2-pyrimidineamine (4) (204 mg, 1 mmol) and ammonium hydroxide (15 ml) were charged to a sealed tube and ethanol (1.5 ml) added. The tube was heated at 100 C. for 24 hours. The solution was concentrated. The residue was absorbed on silica gel and chromatographed (elution with ethyl acetate), yielding (5) as a white powder (118 mg, 65%): MS (70 eV, EI) m/z (relative intensity) 162 (M+, 100), 43 (92), 164 (33), 127 (29), 135 (16). Exact Mass Calcd for C4 H4 N4 ClF: 162.0108. Found: 162.0100.

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, 15598-33-1, 4,6-Dichloro-5-fluoropyrimidin-2-amine.

Reference:
Patent; The Upjohn Company; US5373012; (1994); A;,
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Pyrimidine – Wikipedia

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. 87253-62-1, name is 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. name: 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid

General procedure: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

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, 87253-62-1, 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
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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. 99420-75-4, name is 5-Methylpyrimidine-2-carboxylic acid, molecular formula is C6H6N2O2, 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. Recommanded Product: 99420-75-4

To a solution of 5-methylpyrimidine-2-carboxylic acid (102 mg, 0.742 mmol) and diisopropylethylamine (288 mg, 2.226 mmol) in tetrahydrofuran (4 ml_) at 20 C was added 1 -[b/s(dimethylamino)methylene]- 7/-/-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (423 mg, 1 .1 13 mmol). The reaction mixture was stirred for 20 minutes before a solution of 5-(3-fluorobenzyl)pyridin-2-amine (150 mg, 0.742 mmol) in tetrahydrofuran (1 .0 ml_) was added. The reaction solution was heated to 90 C and stirred for 1 h. The volatiles were removed under reduced pressure and the residue was added to a mixture of dichloromethane (50 ml_) and water (50 ml_). The organic layer was collected, dried over sodium sulfate, filtered and concentrated. The crude sample was dissolved in minimal A/,A/-dimethylformamide and purified by prep-HPLC (Boston C18 21 *250 mm 10 pm column. The mobile phase was acetonitrile/10 mM ammonium acetate aqueous solution) to give A/-(5-(3-fluorobenzyl)pyridin-2-yl)-5-methylpyrimidine-2-carboxamide (150 mg, 0.47 mmol, 63%) as a white solid. 1 H NMR (400 MHz, Dimethylsulfoxide-c/6) d 10.44 (s, 1 H), 8.90 (s, 2H), 8.34 (s, 1 H), 8.19 (d, J = 8.0 Hz, 1 H), 7.79 (q, J = 2.6 Hz, 1 H), 7.34 (q, J = 2.6 Hz, 1 H), 7.01 -7.14 (m, 3H), 3.99 (s, 2H), 2.40 (s, 3H); LCMS (ESI) m/z: 323.0 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 99420-75-4.

Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
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Pyrimidine – Wikipedia

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. 83942-10-3, name is 4,5-Dichloro-6-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4,5-Dichloro-6-methylpyrimidine

PREPARATIVE EXAMPLE 4 5-chloro-6-methyl-4-[N-methyl-2-(2-methyl-4-n-propylphenoxy)ethylamino]pyrimidine (compound number 166) To a solution of 3.2 g (0.02 mol) of 4,5-dichloro-6-methylpyrimidine were added 2.0 g (0.02 mol) of triethylamine and 4.7 g (0.02 mol) of N-methyl-2-(2-methyl-4-n-propylphenoxy)ethylamine, and the mixture was melt-reacted by heating it for 5 minutes on a heater. Upon completion of the reaction, 100 ml of benzene were added to the reaction mixture, and insoluble matters were filtered off. The filtrate was washed with water, dried over anhydrous sodium sulphate, and the benzene distilled off under reduced pressure, leaving an oil. The oil was isolated by column chromatography (Wakogel C-200, eluted with a 3:1 by volume mixture of benzene and ethyl acetate) to give 6.1 g of the desired product in the form of a pale yellow oil nD23.8 1.5632

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, 83942-10-3, 4,5-Dichloro-6-methylpyrimidine.

Reference:
Patent; Sankyo Company, Limited; Ube Industries, Limited; US4435402; (1984); A;,
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Pyrimidine – Wikipedia

Related Products of 17180-94-8 ,Some common heterocyclic compound, 17180-94-8, molecular formula is C4H3ClN2, 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.

General procedure: Under argon protection, NiCl2·6H2O (0.05mmo 1,11.9mg), dppf (0.06mmol, 33.3mg), Zetan (0·2mmol, 13.0mg), DMAP (1.0mmol, 122.2mg), Zetan(CN)2 (0.8mmol) , 93.9mg),p-Chloroanisole (1.0 mmol, 140.6 mg) and acetonitrile (5.0 mL) were sequentially added in a 25.0 mL sealed tube, then directly put it into the oil bath at 60 C, and heating was stopped after 6h, and cooled to room temperature, the reaction solution was directly filtered through a short silica gel column, washed with dichloromethane, concentrated and purified by silica gel column chromatography( given that the product is most easily pulled out, in order to avoid loss of sample mix, unless otherwise noted, both are wet method). Eluent: petroleum ether / ethyl acetate = 20:1, the product was 117.2 mg as a white solid, yield 88%, and 1H NMR purity was greater than 98%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17180-94-8, its application will become more common.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Liu Yuanhong; Zhang Xingjie; (34 pag.)CN108623495; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 23132-67-4, name is 6-Methoxy-2-methylpyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 6-Methoxy-2-methylpyrimidin-4-amine

EXAMPLE 4 (7-methoxy-5-methyl-imidazo[1,2-c]pyrimidin-2-yl)-phenylmethanone A stirred solution of 2.1 g of 6-methoxy-2-methyl-4-pyrimidinamine in dry tetrahydrofuran was treated with a solution of 5.4 g of 3-bromo-1-phenyl-1,2-propanedione in 5 ml of dry ether. After stirring overnight, the mixture was chilled and the precipitated salt filtered off. A suspension of the salt in dry ethanol was refluxed for 1.5 hours, chilled, and filtered. The solid was shaken with a mixture of chloroform and aqueous sodium bicarbonate and the organic layer was evaporated to dryness under reduced pressure. The residue was chromatographed in ethyl acetate on silica to obtain 2.7 g of (7-methoxy-5-methyl-imidazo[1,2-c]pyrimidin-2-yl)-phenylmethanone as a yellow crystalline solid melting at 165-7 C.

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, 23132-67-4, 6-Methoxy-2-methylpyrimidin-4-amine.

Reference:
Patent; Tully; Wilfred R.; US4643999; (1987); A;,
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Pyrimidine – Wikipedia