Tag: M.W:200-300

Synthetic Route of 33097-11-9, 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. 33097-11-9, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde, molecular formula is C6H4Cl2N2OS, 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.

Example 4; 4-Chloro-2-methylsulfinyl-8-(“4-trifluoromethyl-phenvD-8H- pyridor23-Patent; GLAXO GROUP LIMITED; WO2006/104917; (2006); A2;,
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Application of 151266-23-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 151266-23-8 as follows.

Example 13. l-(4-(4-amino-l-cyclopentyl-lH-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)-3- (3-(trifluoromethyl)phenyl)urea (AD60); [0182] A synthetic strategy for Cmpd AD60 is depicted in Scheme 8 following. Scheme 8[0183] Reagent 3-iodo-lH-pyrazolo[3,4-d]pyrimidin-4-amine) (0.5g; 1.9 mmol; Apsel et al., 2008, Id.) was combined with cyclopentyl iodide (0.24 mL; 2.1 mmol), l .Og K2CO3, in 20 mL DMF and heated to 45 C under argon for 2 hours. The reaction was filtered to remove solid K2CO3, and the filtrate was combined with brine and the organic product was extracted in CH2Cl2 (3x 50 mL). The combined organic layer was concentrated in vacuo and purified by silica gel chromatography (MeOH/Chloroform; 5:95) to afford l-cyclopentyl-3- iodo-lH-pyrazolo[3,4-d]pyrimidin-4-amine (ESI-MS m/z [M+H]+ found 330.0, calculated 330.0). 4-nitrophenyl boronic acid (190 mg, 1.1 mmol; Sigma-Aldrich), was coupled to 1- cyclopentyl-3-iodo-lH-pyrazolo[3,4-d]pyrimidin-4-amine (150mg, 0.456 mmol) via the Suzuki reaction in 6 mL 1,2 methoxy ethane, 1 mL of saturated sodium carbonate, 1.65 mL EtOH, and 200 mg of polymer-bound tetrakis palladium. The reaction was stirred under argon for 12 hours at room temperature, filtered through Whatman paper to remove palladium, mixed with brine, extracted in chloroform and the product was subsequently purified on silica in EtOAc and concentrated in vacuo. The purified solid l~cyclopentyl-3-(4- nitrophenyl)-lH-pyrazolo[3,4-d]pyrimidin-4-amine (ESI-MS m/z [M+H]+ found 325.0, calculated 325.1 ; lOOmg, 0.31 mmol) was combined with Zinc dust (605 mg, 9.25 mmol), 10 mL THF, 0.35 mL HOAc for 12 hours at room temperature under Argon. The reaction was filtered through CeIi te, extracted with EtOAc and concentrated in vacuo to yield 3-(4- aminophenyl)-l -cyclopentyl- lH-pyrazolo [3, 4-d]pyrimidin-4-amine (ESI-MS m/z [M+H]+ found 295.0, calculated 295.2). To this reduced product, molar equivalents of3-(trifluoromethyl)phenyl isocyanate (Sigma-Aldrich) were added dropwise in ice-cold CH2C12. The reaction proceeded until completion as judged by TLC, was concentrated in vacuo, resuspended in 50:50 H20-CH3CN, and purified on a Cl 8 column in CH3CN/H20/0.1%TFA (1-100% gradient) to yield AD60 l-(4-(4-amino-l -cyclopentyl- IH- pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea (ESI-MS m/z [M+H]+ found 482.2, calculated 482.0).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,151266-23-8, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; DAR, Arvin; SHOKAT, Kevan M.; WO2010/45542; (2010); A2;,
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Electric Literature of 101803-06-9, 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 101803-06-9, name is 5-Iodo-2-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 1-(2-Deoxy-beta-D-Ribofuranosyl)-5 -(1-propynyl)-2-pyrimidinone 31.67 g (0.13 mol) of 5-iodo-2-methoxypyrimidine, 0.73 g (2.9 mol %) of CuI and 1.02 g (1.1 mol%) of bis(triphenylphosphine)PdCl2 were suspended in 200 ml of anhydrous triethylamine (distilled over BaO) in Parr pressure bottle. The bottle was evacuated and filled with 85% propyne. The bottle was repeatedly shaken and filled with propyne until the pressure had stabilized at 20 psi, and then the mixture was shaken, in a Parr hydrogenator, for 24 hours. More propyne was added at this time shaking was continued for an additional 48 hours. On tlc (methylene chloride), there was only one major product; no starting material was observed. The mixture was diluted with methylene chloride (300 ml), washed with saturated bicarbonate solution (2*60 ml), dried over magnesium sulfate and concentrated to a minimum volume with attendant precipitation. Petroleum ether was added to the mixture and after cooling, the first crop was obtained by filtration. The filtrate was concentrated to give a second crop. Both crops were dried and sublimed at 0.3 mm Hg (max. oil bath temp. 100 C.) to yield 15.26 g (76.7%) of analytically pure, white-crystalline material, 2-methoxy-5-(1-propynyl)pyrimidine; mp 88-89.5 C.).

According to the analysis of related databases, 101803-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Research Foundation of State University of New York; US4895937; (1990); A;,
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Related Products of 36822-08-9 ,Some common heterocyclic compound, 36822-08-9, molecular formula is C10H6N2OS, 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.

Benzo[4,5]thieno[3,2-d]pyrimidin-4(3H)-one (10.78 g, 26.7 mmol) was treated with pyridine (2.68 mL, 33.3 mmol) and phosphoryl trichloride (53.4 mL, 573 mmol), then heated to reflux at 110C for 1 hr. Excess POCl3 was removed and cautiously quenched with ice water in an ice bath. The pH was adjusted to ?5 with ammonium hydroxide. Solid was collected by filtration washed with water. The solid was dried to give 4-chlorobenzo[4,5]thieno[3,2-d]pyrimidine (10 g, 85% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,36822-08-9, its application will become more common.

Reference:
Patent; Universal Display Corporation; Xia, Chuanjun; Joseph, Scott; EP2826781; (2015); A1;,
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Related Products of 1337532-51-0, 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. 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C7H7BrN4, 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.

Add Pd(II) acetate (635 mg, 2.83 mmol), cataCXium A (2.03 g, 5.65 mmol), and aqueous saturated NaHC03(186 mL, 188 mmol) to a suspension of 5-bromo-7- methyl-pyrrolo[2,3-d]pyrimidin-4-amine (21.4 g, 94.3 mmol) and 3-methyl-4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (28.6 g, 123 mmol) in 2-methyl- tetrahydrofuran (214 mL) at 23 C, and stir the mixture in a sealed tube at 100 C for 3 h. Cool to 23 C, filter through a pad of diatomaceous earth, and rinse the solid with H20 (50 mL) and ethyl acetate (100 mL). Separate the organic layer, wash it with aqueous saturated NaCl (50 mL), and concentrate under reduced pressure. Purify the residue by chromatography (eluent: hexane / acetone 0-100%) to obtain the title compound (12.1 g, 51%) as a yellow solid. ES/MS m/z 254.1 (M+H)

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 1337532-51-0, 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine.

Reference:
Patent; ELI LILLY AND COMPANY; CIFUENTES-GARCIA, Marta Maria; GARCIA-PAREDES, Maria Cristina; (34 pag.)WO2018/194885; (2018); A1;,
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Synthetic Route of 343-67-9, 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 343-67-9, name is Ethyl 4-hydroxy-2-(trifluoromethyl)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate B2-Ethyl 2-trifluoromethyl-4-chloropyrimidine-5-carboxylate To a solution of ethyl 4-hydroxy-2-trifluorormethylpyrimidine-5-carboxylate (51.8 g) in dichloromethane (600 ml) cooled in an ice bath was added oxalyl chloride (57.4 ml) followed by dimethylformamide (0.2 ml).The mixture was stir at room temperature for 16 h and then evaporated.toluene was added and evaporated.The residue was dissolved in dichloromethane, washed with water, dried (MgSO4) and evaporated to give the title compound as an orange oil (55.7 g, 100%).1H-NMR (CDCl3) delta 9.25 (1H, s), 4.51 (2H, q), 1.46 (3H, t); 13C-NMR (CDCl3) delta 126.0 (2C), 161.1, 158.1 (q, J=39 Hz), 127.0, 118.9 (q, J=276 Hz), 63.5, 14.4.

According to the analysis of related databases, 343-67-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SmithKline Beecham p.l.c.; US2004/167142; (2004); A1;,
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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. 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C6H3BrClN3

To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (obtained in Reference Example 8(1); 2.00 g) in tetrahydrofuran (50 mL) was added dropwise under nitrogen atmosphere at -65C 2.64M butyllithium-hexane solution (7.2 mL), and then the mixture was stirred for 30 minutes. To the reaction mixture was added a solution of ethyl chloroformate (905 muL) in tetrahydrofuran (5 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and then the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (solvent; hexane/ethyl acetate = 65/35 to 20/80) to give 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid ethyl ester (1.43 g) as a colorless solid (yield: 74%). MS(APCI)m/z; 226/228[M+H]+.

The synthetic route of 22276-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP2390254; (2011); A1;,
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Related Products of 126728-20-9, Adding some certain compound to certain chemical reactions, such as: 126728-20-9, name is 2,4-Dichloropyrido[2,3-d]pyrimidine,molecular formula is C7H3Cl2N3, 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 126728-20-9.

Compound a (432 mg, 1.1 eq), b-2 (600 mg, 1.1 eq),Aluminum trichloride (382.4 mg, 1 eq) was added to a 50 mL eggplant bottle and reacted at 80 C. The reaction was completed by TLC, and then stirred with ice water for 5 min.Filter by suction and rinse the filter cake with 50 mL of water.The intermediate c-2 was isolated by column chromatography, and the yield of 400 mg was 46%.

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. 126728-20-9, 2,4-Dichloropyrido[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Liaoning University; Chen Ye; Ding Shi; Liu Ju; Ji Jingchao; Hao Xuechen; Liu Yutong; Li Jie; Zhang Mingjuan; Gong Yilin; (29 pag.)CN110283162; (2019); A;,
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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. 1088994-22-2, name is 5-Methyl-2-(pyrimidin-2-yl)benzoicacid. A new synthetic method of this compound is introduced below., COA of Formula: C12H10N2O2

5-Methyl-2-(pyrimidin-2-yl)benzoic acid (1.47 g; 6.86 mmol) is dissolved in DCM (50 ml) anddimethylaminopyridine (168 mg, 1.37 mmol) and EDC (1.45 g; 7.55 mmol) are added.Stirring is continued for 30 minutes followed by the addition of (S)-5-bromo-7-methyl-2-(2-methylpyrrolidin-2-yl)-1H-benzo[d]imidazole hydrochloride (2.27 g; 6.86 mmol). Stirring at RT is continued for 16 hours. Ethylacetate (150 ml) and sat. sodium hydrogencarbonate solution (100 ml) are added to the reaction mixture. The phases are separated and the aq. phase is extracted with EtOAc (50 ml). The combined organic layers are dried with Mg504, filteredand the solvent is evaporated under reduced pressure. The product is purified by preparative HPLC (conditions C) to give 2.07 g of the title compound as a white powder; tR [mm] = 0.73; [M+H] = 492.14.

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, 1088994-22-2, 5-Methyl-2-(pyrimidin-2-yl)benzoicacid.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BOSS, Christoph; BRISBARE-ROCH, Catherine; BROTSCHI, Christine; GUDE, Markus; HEIDMANN, Bibia; JENCK, Francois; SIFFERLEN, Thierry; STEINER, Michel; WILLIAMS, Jodi; WO2015/83094; (2015); A1;,
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Application of 4359-87-9, 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. 4359-87-9, name is 2,4,6-Trichloro-5-nitropyrimidine, molecular formula is C4Cl3N3O2, 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.

To a solution of 2,4,6-trichloro-5-nitropyrimidine (9.0 g, 39.4 mmol) in THF (540 mL) was added an ammonia solution (10.8 mL, 10 N in EtOH, 78.8 mmol) dropwise at -70 C. After the reaction was stirred at -70 C for 30 mm, it was acidified with AcOH (pH 45) and concentrated. The residue was diluted with EtOAc and the resulting mixture was stirred for 30 mm and filtered. The solids were washed with EtOAc and the organics were combined and concentrated to afford the title compound (16a) (8.0 g, 97%), which was directly used for the next step without further purification.

According to the analysis of related databases, 4359-87-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORIC PHARMACEUTICALS, INC.; DU, Xiaohui; EKSTEROWICZ, John; FANTIN, Valeria R.; JACKSON, Erica L.; SUN, Daqing; YE, Qiuping; MOORE, Jared; ZAVOROTINSKAYA, Tatiana; (262 pag.)WO2019/90111; (2019); A1;,
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