Pyrimidines

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.130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, molecular formula is C11H15ClN2O2, molecular weight is 242.7, as common compound, the synthetic route is as follows.Application In Synthesis of 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one

3-(2-chloroethyl-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[l,2-a]pyrimidin-4-one (60 gm, 0.165 mole) was added to acetonitrile (300 ml) at 25-350C and stirred for 10 mins at 25-35C. 6-Fluoro-3-piperidin-4-yl-benzo[d]isoxazole.HCl (55.9 gm,0.218 mole) and sodium carbonate anhydrous (78.8 gm, 0.743 mole) was added to the reaction mass. The reaction mass was then stirred for 10 min at 25-35C and temperature was raised to 60-65C. The reaction mass was then maintained at 60-65C for 30-45 hrs, slowly cooled and maintained at 25-35C for 1 hr. The resultant solid was filtered and treated with water (600 ml) for 1 hr. The solid was again filtered, washed with water and IPA and dried at 40-45C to give 85 gm of Form II of paliperidone.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,130049-82-0, 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, and friends who are interested can also refer to it.

Reference:
Patent; MATRIX LABORATORIES LIMITED; WO2009/44413; (2009); A2;,
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Pyrimidine – Wikipedia

Electric Literature of 22536-61-4 , The common heterocyclic compound, 22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, 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 50 mL round bottom flask was added 2-chloro-5-methylpyrimidine (0.150 g, 1.167 mmol), clinfloxacin.(0.427 g, 1.167 mmol) and potassium carbonate (0·193 g, 1 · 400 mmol), then 10 mL of acetonitrile, refluxed at 80 C 23 hours. After the reaction,The reaction mixture was concentrated under reduced pressure.Get a crude product,Use it again(methanol / dichloromethane,1/10, V/V) Purified by silica gel column chromatography,get 0.329g Compound III-2, a yellow solid.Yield: 71.8%

The synthetic route of 22536-61-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southwest University; Zhou Chenghe; Li Di; Chen Jinping; Ba Tini·nasaiya; An Sali·muhanmode·fuade; (19 pag.)CN109942546; (2019); A;,
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Electric Literature of 2434-53-9, 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. 2434-53-9, name is 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

General procedure: 7 (2.0 mmol, 0.38 g) and the corresponding amine (2.0 mmol) were placed in pressure tube under the flow of dry argon and dissolved in dry DMF (10 mL) containing 1 mL of TMSCl. The mixture was heated at 100 C during 2-12 h (controlled by TLC). Then this solution was evaporated under reduced pressure, treated with water, filtrated and dried on the air and recrystallized from an appropriate solvent, or was subjected to a column chromatography over silica gel.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2434-53-9, 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Article; Iaroshenko, Viktor O.; Vilches-Herrera, Marcelo; Gevorgyan, Ashot; Mkrtchyan, Satenik; Arakelyan, Knar; Ostrovskyi, Dmytro; Abbasi, Muhammad S.A.; Supe, Linda; Hakobyan, Ani; Villinger, Alexander; Volochnyuk, Dmitriy M.; Tolmachev, Andrei; Tetrahedron; vol. 69; 3; (2013); p. 1217 – 1228;,
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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. 1134327-91-5, name is Ethyl 2-(5-bromopyrimidin-2-yl)acetate. A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 2-(5-bromopyrimidin-2-yl)acetate

To a solution of ethyl 2-(5-bromopyrimidin-2-yl)acetate (S2, 1 equiv) in DMF/H2O (9:1, 10 vol) was added compound S1 (1 equiv), K2CO3(2 equiv), and tetrakis(triphenylphosphine)palladium (0.1 equiv). The reaction mixture was stirred at 90 C. for 5 h and then concentrated under reduced pressure. The remaining residue was purified by column chromatography on silica gel to give compound S3.

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, 1134327-91-5, Ethyl 2-(5-bromopyrimidin-2-yl)acetate.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
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Pyrimidine – Wikipedia

Application of 144927-57-1, Adding some certain compound to certain chemical reactions, such as: 144927-57-1, name is Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate,molecular formula is C9H8ClN3O2, 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 144927-57-1.

To a stirred solution of ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (4.00 g,17.7 mmol) in DCM (40 mL) was added triethylamine (7.48 mL,53.3 mmol) and N,N-dimethylaminopyridine (0.210 g,1.77 mmol) at room temperature. Benzene sulfonyl chloride (4.00 g,22.9 mmol) was then added dropwise over 10 min. The resulting reaction mixture was stirred at room temperature for another 30 min. After completion of reaction,the reaction mixture was diluted with DCM (50 mL) and washed with water. The organic layer was then washed with brine and dried over anhydrous sodium sulfate. The organic layer was filtered and concentrated under vacuum to provide crude material which was then purified by Combi-flash purifier with 20% ethyl acetate in hexane as an eluent to afford ethyl 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate as a light yellow solid: (5.3 g,82% yield): MS (ES) m/z 366.3(M+H)+1.

According to the analysis of related databases, 144927-57-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACLARIS THERAPEUTICS, INC.; JACOBSEN, Eric Jon; ANDERSON, David Randolph; BLINN, James Robert; HOCKERMAN, Susan Landis; HEIER, Richard; MUKHERJEE, Paramita; (196 pag.)US2020/48262; (2020); A1;,
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Reference of 2927-71-1, 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. 2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine, molecular formula is C4HCl2FN2, 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.

Preparation of compound 55a: 2-chloro-5-fluoro-4-methoxypyrimidine2,4-Dichloro-5-fluoropyrimidine (515 mg, 3.08 mmol) was weighed into a 150 mL RBF, and was suspended in THF (5.0 mL). The stirring suspension was cooled to -10 C. NaOMe (250 mg, 4.63 mmol) was added in one portion at -10 C. An additional 0.5 eq of NaOMe were added and the suspension was stirred at RT for 21 h. The suspension was diluted with MeOH, and the the solvents were removed in vacuo. The crude material was purified by flash chromatography (eluting with 100%o DCM) to give 2-chloro-5- fluoro-4-methoxypyrimidine (37 mg, 0.228 mmol, 7.38 %> ) as an amorphous white solid. MS (ESI, pos. ion) m/z: 162.9 (M+l). .H NMR (400 MHz, DMSO-d6) delta ppm 8.60 (d, J=2.7 Hz, 1 H), 4.04 (s, 3 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 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine.

Reference:
Patent; AMGEN INC.; WANG, Hui-Ling; CEE, Victor, C.; HERBERICH, Bradley, J.; JACKSON, Claire, L., M.; LANMAN, Brian, Alan; NIXEY, Thomas; PETTUS, Liping, H.; REED, Anthony, B.; WU, Bin; WURZ, Ryan; TASKER, Andrew; WO2012/129338; (2012); 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.13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine, molecular formula is C5HCl2N3S, molecular weight is 206.0525, as common compound, the synthetic route is as follows.Computed Properties of C5HCl2N3S

A 10 mL round-bottom flask, was charged withcompound 45.3 (500 mg, 2.27 mmol, 1.00 equiv) and acetic acid-d4 (5 mL). The reaction was stirred for 24 hours at 110 C. The solids were filtered out and solvents were removed under reduced pressure to provide 450 mg (89%) of intermediate 58.1 as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13479-88-4, 5,7-Dichlorothiazolo[5,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine; WO2015/48281; (2015); A1;,
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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. 26452-81-3, name is 4-Chloro-6-methoxypyrimidine. A new synthetic method of this compound is introduced below., Safety of 4-Chloro-6-methoxypyrimidine

Example 1 90 parts by weight of phosphorus oxychloride and 10 parts by weight of 4-chloro-6-methoxypyrimidine were introduced into a stirred vessel. The mixture was heated with stirring to 100° C. and, at this temperature, 6 parts by weight of water were metered in at a constant rate over the course of 4 hours. The mixture was then stirred at 100° C. for 1 hour. After cooling to room temperature, 99.6 parts by weight of a reaction mixture whose HPLC analysis showed contents of 0.2percent 4-chloro-6-methoxypyrimidine and 9.3 parts by weight of 4,6-dichloropyrimidine were obtained.

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, 26452-81-3, 4-Chloro-6-methoxypyrimidine.

Reference:
Patent; Bayer Akitnegesellschaft; US6441170; (2002); B1;,
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Pyrimidine – Wikipedia

Application of 2927-71-1, 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 2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 1; 2-Chloro-5-fluoro-N-(5-methyl-lH-pyrazol-3-yl)pyrimidin-4-amineTo a solution of 5-methyl-lH-pyrazol-3-amine (612 mg, 6.0 mmol) in absolute EtOH (10 ml) was added triethylamine (1.1 ml) and 2,4-dichloro-5-fluoropyrimidine (1.0 g, 6.0 mmol) and the resulting solution was aged at room temperature for 12 hours. The mixture was partitioned between EtOAc and water. The organic layer was washed with brine and dried. The solvents were removed under reduced pressure to give the title compound as a solid (679 mg). LC-MS: 228 [M+eta].

According to the analysis of related databases, 2927-71-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/7753; (2009); A2;,
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Pyrimidine – Wikipedia

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. 4316-94-3, name is 6-Chloro-5-nitropyrimidin-4-amine. A new synthetic method of this compound is introduced below., Computed Properties of C4H3ClN4O2

4-Amino-5-nitro-6- chloropyrimidine (5.0 g, 29 mmol), 4-(l-aminoethyl)phenol (4.3 g, 32 mmol) and Et3N (4.5 mL, 3.2 g, 32 mmol) were combined in anhydrous DMF (30 mL). After stirring 2 h at 25 0C, the mixture was poured into dilute citric acid (150 mL; pH ca. 3) and the precipitated product was collected by suction filtration and washed with H2O. The solid was recrystallized from a refluxing mixture Of H2O (100 mL) and EtOH (50 mL) to yield 6.6 g (84%).

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, 4316-94-3, 6-Chloro-5-nitropyrimidin-4-amine.

Reference:
Patent; DOW AGROSCIENCES LLC; BREWSTER, William; DEMETER, David; ERICKSON, W.; LOWE, Christian; KLITTICH, Carla; NUGENT, Jaime; RIEDER, Brent; SIDDALL, Thomas; YAO, Chenglin; YERKES, Carla; ZHU, Yuanming; WO2011/25505; (2011); A1;,
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