Tag: M.W:200-300

Synthetic Route of 114040-06-1, Adding some certain compound to certain chemical reactions, such as: 114040-06-1, name is 3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine,molecular formula is C6H2BrCl2N3, 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 114040-06-1.

To a solution of 3-bromo-5,7-dichloropyrazolo [1,5-a] pyrimidine (0.14 g, 0.53 MMOL) in ethanol (20 cm3) was added 4-AMINO-N, N- dimethbenzenesulphonamide (0.107 g, 0.53 mmol). The reaction was heated at reflux for 16 h. The reaction was concentrated in vacuo and the residue triturated with hot ETHANOL (2 X 10 CM3) to yield the product as a white solid (0. 10 G, 43%). 8H (400 MHz; D4-CDC13) 8.10 (1H, s), 7.89 (2H, d, J 6.7), 7.66 (2H, d, J6. 7), 6.51 (1 H, s), 2.74 (6H, s). M/Z430, 432 and 434 each (M+H, 75 %, 100% and 25%), retention time 2. 58 min (Method A).

According to the analysis of related databases, 114040-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERNALIS (CAMBRIDGE) LIMITED; WO2004/87707; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1122-44-7 , The common heterocyclic compound, 1122-44-7, name is 4-Amino-5-iodopyrimidin-2(1H)-one, molecular formula is C4H4IN3O, 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.

To a stirred solution of 4-amino-5-iodouracil (200 mg, 0.84 mmol) in anhydrous dimethylformamide (15 mL) at room temperature in a nitrogen atmosphere were added tetrakis (triphenyl phosphine)palladium (98 mg, 0.08 mmol), copper(I)iodide (32 mg, 0.17 mmol), diisopropylethylamine (0.28 mL, 1.7 mmol) and 1-phenylacetylene (0.33 mL, 2.53 mmol). The reaction mixture was stirred at room temperature. After 22 h, 10 drops of 5% of the disodium salt of EDTA/H2O were added to the reaction mixture, and the mixture was concentrated in vacuo. The residue obtained was purified on silica gel column using MeOH/CHCl3 (4:96, v/v) as an eluent to give 7. This was obtained as a solid in 67% yield; mp > 250 C; 1H NMR (DMSO-d6): delta 6.93 (s, 1H, NH2), 7.40 (m, 3H, C6H5), 7.60 (m, 2H, C6H5), 7.66 (s, 1H, NH2), 7.83 (s, 1H, H-6), 11.01 (br s, 1H, NH); 13C NMR (DMSO-d6): delta: 56.48 (C-beta), 82.30 (C-alpha), 94.18 (C-5), 128.75, 128.90, 131.61 (C-phenyl), 147.30 (C-6), 155.52 (C-2), 165.30 (C-4). FTIR (KBr) cm-1: 3461 (Ar C-H), 3399 (NH), 3139 (NH2), 2219 (C?C), 1890, 1657 (C=O), 1457, 1230, 1027, 911, 749, 687, 559 cm-1. Anal. C12H9N3O (M.W. 211.12). Calcd C 68.24, H 4.29, N 19.8. Found C 68.64, H 4.57, N 19.51.

The synthetic route of 1122-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Garg, Gaurav; Pande, Milind; Agrawal, Ambika; Li, Jie; Kumar, Rakesh; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1771 – 1777;,
Pyrimidine | C4H4N2 – PubChem,
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Synthetic Route of 1209459-80-2, 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. 1209459-80-2, name is Methyl 6-bromopyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below.

Tripotassium phosphate (2eq) was added in one portion to a stirred solution of 8-chloro-6-(4,4,5,5-tetramethyl- [l,3,2]dioxaborolan-2-yl)-chroman (leq) and methyl 4-bromopyridine-2-carboxylate (2eq) in DMF (lOvol). The mixture was degassed with nitrogen for 5 minutes, after which time Pd(dppf)2C12 (0.2eq) was added in one portion, the mixture was then heated to 60oC and stirred at this temperature for 16 hours under a nitrogen atmosphere. After this time the reaction mixture was cooled to room temperature and partitioned between ethyl acetate (5 vol) and water (5 vol). The organic layer was separated, washed sequentially with water (5vol) then brine (5vol) before being dried (MgS04), filtered andconcentrated. The resulting residue was purified using a Biotage Isolera (lOOg silica column eluting with a gradient from 0% heptane to 80% DCM / 20% heptane) to give the desired compound as a white solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1209459-80-2, Methyl 6-bromopyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; COURTNEY, Stephen Martin; PRIME, Michael; MITCHELL, William; BROWN, Christopher John; DE AGUIAR PENA, Paula C.; JOHNSON, Peter; DOMINGUEZ, Celia; TOLEDO-SHERMAN, Leticia M.; MUNOZ, Ignacio; WO2013/33085; (2013); A1;,
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Application of 3438-55-9, 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. 3438-55-9, name is 5-Bromo-4-chloro-6-methylpyrimidine. A new synthetic method of this compound is introduced below.

PREPARATIVE EXAMPLE 6 dl-5-bromo-6-methyl-4-(alpha-methylbenzylamino)pyrimidine (compound number 314) 2.0 g (0.02 mol) of triethylamine and 2.4 g (0.02 mol) of dl-alpha-methylbenzylamine were added to a solution of 4.15 g (0.02 mol) of 5-bromo-4-chloro-6-methyl-pyrimidine in 50 ml of benzene, and the mixture was refluxed with stirring for 5 hours. Upon completion of the reaction, the reaction product was washed with water, dried over anhydrous sodium sulphate and the benzene was distilled off to leave an oil. This oil was then caused to crystallize using column chromatography (Wakogel C-200, eluted with a 1:1 mixture of benzene and ethyl acetate). Crystals were obtained and recrystallized from n-hexane to give 2.6 g of the desired product in the form of pale yellow prisms melting at 85-87 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3438-55-9, its application will become more common.

Reference:
Patent; Sankyo Company, Limited; Ube Industries, Limited; US4435402; (1984); A;,
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Application of 87789-35-3, 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 87789-35-3, name is 5,7-Dichloro-2-(methylthio)thiazolo[4,5-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of ethyl 5-chloro-2-(methylthio)thiazolo[4,5-d]pyrimidine-7-carboxylate: The title compound was prepared from 5,7-dichloro-2-(methylthio)thiazolo[4,5-d]pyrimidine (commercially obtained from Combi-Block, San Diego, CA) using chemistry similar to that described in Example 1. ESI MS: m/z [M+H+] for C9H8ClN3O2S2, calcd 290.0, found 290.1.

According to the analysis of related databases, 87789-35-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Corvus Pharmaceuticals, Inc.; LI, Zhihong; FILONOVA, Lubov, Konstantinovna; VERNER, Erik; (375 pag.)EP3616753; (2020); A1;,
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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. 313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 313339-35-4

To a mixture of 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carboxylic acid (1.50 g) and dichloromethane (15 mL), oxalyl chloride (1.20 mL) and DMF (0.015 mL) were added under ice cooling and stirred 30 minutes under ice cooling and 2 hours at room temperature. The solvent was distilled off under reduced pressure, followed by an azeotropic process with toluene. The resulting residue was dissolved in THF, followed by dropwise addition of 40% aqueous methylamine at -10 C. After the dropwise addition was completed, the reaction liquid was concentrated, and water was added. The resulting solid was collected by filtration and washed with water to give a white solid. The solid was dissolved in ethyl acetate, washed with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off. To a mixture of the resulting residue and dioxane (20 mL), 3-(methylsulfonyl)aniline hydrochloride (432 mg) and N,N-diisopropylethylamine (0.73 mL) were added and stirred at 100 C. for 4 hours. After cooling, the reaction liquid was diluted with ethyl acetate and washed with saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent; chloroform_methanol=100:0 to 30:1) to give 4-chloro-N-methyl-2-(methylsulfanyl)-6-{[3-(methylsulfonyl)phenyl]amino}pyrimidine-5-carboxamide (445 mg) as a white solid

The synthetic route of 313339-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Waters Technologies Corporation; US2012/40968; (2012); A1;,
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Related Products of 4319-87-3, 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.4319-87-3, name is 5-Bromo-4-methoxy-6-methylpyrimidine, molecular formula is C6H7BrN2O, molecular weight is 203.04, as common compound, the synthetic route is as follows.

A mixture of 4-[3-methyl-4-(4,4,5,5-tetram ethyl-i ,3,2-d ioxaborolan-2-yl)phenoxy]furo[3,2- c]pyridine (C2) (4.0 g, ii mmol), 5-bromo-4-methoxy-6-methylpyrimidine (Z. Wang et al., Synthesis2Oll, 1529-1531)(2.Og, 10 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (1.1 g, 1.4 mmol) and potassium carbonate (4.0 g, 29 mmol) in 1 ,4-dioxane (30 mL) containing 5 drops of water was heated at 120 00 for 2 hours. After filtration and concentration of the filtrate under reduced pressure, the residue was purified by silica gel chromatography (Eluent: 33% ethyl acetate in petroleum ether) to give the product as a yellow solid. Yield: 1.8 g, 5.2 mmol, 52%. 1H NMR (400 MHz, ODd3) oe8.72 (s, 1H), 8.07 (d, J=6.0 Hz, 1H), 7.66 (d, J=2.3 Hz, 1H), 7.25 (dd, J=5.9, 0.9 Hz, 1H), 7.19-7.21 (m, 1H), 7.09-7.16 (m, 2H), 6.88 (dd, J=2.3, 0.8 Hz, 1H), 3.95 (s, 3H), 2.29 (s, 3H), 2.07 (s,3H).

Statistics shows that 4319-87-3 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-4-methoxy-6-methylpyrimidine.

Reference:
Patent; PFIZER INC.; COE, Jotham, Wadsworth; ALLEN, John, Arthur; DAVOREN, Jennifer, Elizabeth; DOUNAY, Amy, Beth; EFREMOV, Ivan, Viktorovich; GRAY, David, Lawrence, Firman; GUILMETTE, Edward, Raymond; HARRIS, Anthony, Richard; HELAL, Christopher, John; HENDERSON, Jaclyn, Louise; MENTE, Scot, Richard; NASON, Deane, Milford, II; O’NEIL, Steven, Victor; SUBRAMANYAM, Chakrapani; XU, Wenjian; WO2014/72881; (2014); A1;,
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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.60703-46-0, name is 2,4,6-Trichloro-5-methoxypyrimidine, molecular formula is C5H3Cl3N2O, molecular weight is 213.4491, as common compound, the synthetic route is as follows.Computed Properties of C5H3Cl3N2O

Step 3: Under an atmosphere of nitrogen a solution of 2,4,6-trichloro-5-methoxy- pyrimidine (4.0 g, 18.7 mmol) in DCM (200 mL) was cooled to 0C and treated with boron tribromide (neat, 6.6 mL, 65 mmol) dropwise. After stirring for 18 hours at room temperature LCMS analysis indicated complete reaction. The reaction mixture was cooled and carefully diluted with methanol (25 mL) and the reaction mixture diluted with water (200 mL). The aqueous layer was washed with DCM and the combined organic extracts dried (Na2S04) filtered and concentrated in vacuo to give 2,4,6-trichloro-5-hydroxy-pyrimidine as a pale tan solid (2.55 g, 71%). 13C NMR (DMSO-de): 149.23 (C), 145.25 (C), 145.08 (C). LCMS: RT= 2.65/2.77 [M- H]-= 197/199.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60703-46-0, 2,4,6-Trichloro-5-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA-ROCHE AG; DOTSON, Jennafer; HEALD, Robert Andrew; HEFFRON, Timothy; JONES, Graham Elgin; KRINTEL, Sussie Lerche; MCLEAN, Neville James; NDUBAKU, Chudi; OLIVERO, Alan G.; SALPHATI, Laurent; WANG, Lan; WEI, BinQing; WO2012/82997; (2012); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 163263-91-0, 2,4-Dichloro-6-(4-methoxyphenyl)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, HPLC of Formula: C11H8Cl2N2O, blongs to pyrimidines compound. HPLC of Formula: C11H8Cl2N2O

1H-NMR (300 MHz, CDCl3): delta (ppm) 8.91 (d, J= 3.0 Hz, 1H), 8.76 (m, 4H), 8.39 (d, J = 9.0 Hz, 2H), 7.92 (m, 2H), 7.58-7.38 (t, J = 8.0 Hz, 2H), and 7.06(d, J = 9.0 Hz, 2H), 3.91 (s, 3H); 13C-NMR (75 MHz, DMSO-d6): delta (ppm) 165.2, 163.9, 163.6, 162.1, 155.6,154.4, 150.1, 149.4, 137.1, 136.8, 129.5, 129.2, 125.6, 124.6, 124.1, 122.4, 114.2, 111.1, and 55.4; and LRMS(ESI-MS) m/z = 341.13 [M + H]+In a dry round-bottomed flask, 2,4-dichloro-6-(4-methoxyphenyl)pyrimidine (677 mg, 2.65mmol, 1.0 eq) and Pd(Ph3)4 (460 mg, 0,39 mmol, 0.15 eq) are introduced under argon atmosphere. Dry toluene (20 mL) is added, and a cooling system is installed. The mixture is degassed for 10 min before the addition of 2-(tributylstannyl)pyridine (2.1 mL, 6.63 mmol, 2.5 eq) and heated at reflux (110 C)for 15 h. Then, 30 mL of water is added. The crude mixture is filtrated on a pad of celite and washed with ethyl acetate, followed by extraction. The combined organic phase is dried over MgSO4, filtered and concentrated to dryness. The product is purified by column chromatography (Al2O3-cyclohexane/AcOEt 50/50) to afford the expected product (749 mg, 83%).

The synthetic route of 163263-91-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Morel, Elodie; Beauvineau, Claire; Naud-Martin, Delphine; Landras-Guetta, Corinne; Verga, Daniela; Ghosh, Deepanjan; Achelle, Sylvain; Mahuteau-Betzer, Florence; Bombard, Sophie; Teulade-Fichou, Marie-Paule; Molecules; vol. 24; 3; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 313339-35-4, 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.313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H4Cl2N2O2S, molecular weight is 239.08, as common compound, the synthetic route is as follows.

A 50-mL 3 -necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was charged with a solution of 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid (700 mg, 2.93 mmol, 1.50 equiv) and N,N-dimethylformamide (1 drop) in dichloromethane (10 mL). The solution was treated with oxalyl chloride (750 mg, 5.91 mmol, 3.00 equiv) dropwise with stirring, stirred for 2 h at room temperature and then treated with a solution of Intermediate 2 (800 mg, 1.97 mmol, 1.00 equiv) in dichloromethane (10 mL) and DIE A (2 mL) dropwise with stirring at 0 C. The resulting solution was stirred for an additional 1 h at room temperature, concentrated under vacuum and the residue was purified by chromatography on silica gel (1 : 10 ethyl acetate/petroleum ether) to afford the title compound as a colorless oil. HPLC/MS: 626 (M+H+); Rt 4.78 min (LC4).

The chemical industry reduces the impact on the environment during synthesis 313339-35-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; INTERVET INTERNATIONAL B.V.; GRAHAM, Thomas; SHEN, Dong-Ming; LIU, Wensheng; WU, Zhicai; NARGUND, Ravi, P.; DE VITA, Robert, J.; BALKOVEC, James, M.; YU, Yang; WO2013/68439; (2013); A1;,
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