Pyrimidines

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. 4595-59-9, name is 5-Bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. 4595-59-9

[0745] Synthesis of pyrimidine-5-carbaldehyde: [0746] To a stirred solution of 5-bromopyrimidine (5 g, 31.66 mmol) in THF (50 mL) under argon atmosphere was added n-butyl lithium (2.2 g, 34.83 mmol) drop wise for 10 min at -78 C and stirred for 20 min. To this was added DMF (2.3 g, 31.66 mmol) at -78 C and stirred for 30 min. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution (40 mL) and extracted with EtOAc (3 x 40 mL). The combined organic extracts were washed with water (30 mL), brine (30 mL), dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 25% EtOAc/ Hexanes to afford pyrimidine-5-carbaldehyde (200 mg, 3%) as colorless thick syrup. TLC: 30% EtOAc/ Hexanes (R 0.2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4595-59-9, 5-Bromopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
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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 3934-20-1 as follows., 3934-20-1

Example 1 : 2-Amino-4-chloropyrimidine (2) and 4-amino-2-chloropyrimidine (3) A suspension of 2,4-dichloropyrimidine (7.45 g, 50.0 mmol) in ammonium hydroxide (25%, 125 mL) is stirred at room temperature for 5 h. The appearance of the insoluble material changes from “salt-like” to “snow-like”. The precipitate is collected by filtration and dried in vacuo. The crude material is redissolved in MeOHiCH2CI2 (1 :1), adsorbed on SiO2 and purified by column chromatography (gradient cyclohexane:ethyl acetate from 5:1 to 1 :1) to yield 1.48 g (23%) of 2 and 1.73 g (26%) of 3 (TLC cyclohexane:ethyl acetate 3:1 , Rf (2)=0.45, Rf (3)=0.32). ESI-MS m/z 129.8 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 3934-20-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; COVALYS BIOSCIENCES AG; WO2006/114409; (2006); A1;,
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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 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. This compound has unique chemical properties. The synthetic route is as follows. 130049-82-0

Example 2 Step-I: Preparation of Crude Paliperidone3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]-pyrimidin-4-one (25 g) was added to ethanol (500 ml) at 25-30 C. under stirring. 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (20.1 g) and anhydrous sodium carbonate (38 g) were added to the above solution and then heated to 58-62 C. The resulting mass was stirred for 24 hours at 58-62 C. The reaction mass was cooled to 25 C., the inorganic material was filtered out and the resulting mass was washed with ethanol (75 ml). The ethanol was distilled under vacuum in water bath at 50 C. and the resulting residue was dissolved in methylene dichloride (1250 ml). The methylene chloride solution was washed with water (600 ml) 3 times and then dried with anhydrous sodium sulfate. Sodium sulfate was filtered and methylene dichloride was distilled under vacuum at 30-40 C. After complete distillation of methylene chloride, methanol (75 ml) was added to the residue, stirred for 2 hours, filtered the material and dried at 50 C. under high vacuum to yield 23.0 g of crude paliperidone (HPLC Purity: 95.11%; content of the keto impurity: 0.24 wt %).Step-II: Purification of PaliperidoneCrude paliperidone (23 g, obtained in step-I) was heated with dimethylformamide (115 ml) under stirring at 56 C. for 3 hours. The resulting mass was cooled to 25 C., and material was filtered and washed initially with dimethylformamide (23 ml) followed by methanol (23 ml). The resulting solid was heated to 56 C. with dimethylformamide (69 ml) and the mass was stirred for 3 hours and then cooled to 25 C. The resulting mass was filtered and washed initially with dimethylformamide (23 ml) followed by methanol (23 ml). The resulting solid was stirred with methanol (80 ml) for 3 hours, filtered, washed with methanol (80 ml), and then dried in an air oven at 25 C. for 3 hours to yield 13.6 g of paliperidone. The product was then dissolved in methanol (816 ml) at 65 C. to provide a clear solution and the solution was cooled to 50 C. This procedure was followed by the addition of activated carbon (3.5 gm). The resulting mass was stirred for 30 minutes at 50 C. and then filtered on a Hiflo bed. Sodium borohydride (10 mg) was added to the resulting solution and then stirred for 2 hours at 50 C. followed by distillation of methanol until the paliperidone crystallized out. The resulting solution was cooled to 25 C., filtered the material, washed with methanol and then dried at 60 C. under vacuum to yield 10.7 g of pure paliperidone (HPLC Purity: 99.95%; Content of the keto impurity: 0.035 wt %).; Example 4 Purification of PaliperidoneCrude paliperidone (20 g, obtained in step-I of example 2) was heated with sulfolane (100 ml) under stirring at 60 C. for 3 hours, the resulting mass was cooled to 25 C. The material was filtered and washed initially with sulfolane (20 ml) followed by methanol (20 ml). The filtered solid was slurried with sulfolane (60 ml), the resulting slurry was heated to 60 C. under stirring and then maintained for 3 hours. The resulting mass was cooled to 25 C., filtered the solid and washed initially with sulfolane (20 ml) followed by methanol (20 ml). The filtered solid was stirred with water (200 ml) for 1 hour and then the material was filtered and washed with water (100 ml) followed by methanol (50 ml). The resulting solid was then stirred with methanol (100 ml) for 1 hour, and the material was filtered and washed with methanol (50 ml) and then dried in an air oven at 25 C. for 3 hours to yield 13.3 g of paliperidone. The product was then dissolved in methanol (800 ml) at 65 C. to provide a clear solution. The solution was cooled to 50 C. followed by the addition of silica gel (20 g) with stirring for 30 minutes at 50 C. The resulting solution was filtered to remove the silica gel. Sodium borohydride (10 mg) was added to the resulting filtrate and the temperature was maintained for 2 hours at 50 C. Methanol was distilled until paliperidone crystallized out and the resulting solution was cooled to 25 C. The separated solid was filtered, washed with methanol and then dried at 60 C. under vacuum to yield 11 g of pure paliperidone (HPLC Purity 99.7%; Content of the keto impurity at 0.96 RRT: 0.02 wt %).

Statistics shows that 130049-82-0 is playing an increasingly important role. we look forward to future research findings about 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one.

Reference:
Patent; ACTAVIS GROUP PTC EHF; US2009/247553; (2009); A1;,
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156-81-0, 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. 156-81-0, name is Pyrimidine-2,4-diamine. This compound has unique chemical properties. The synthetic route is as follows.

2-[(2-aminopyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrile (2-3) 2,4-Diaminopyrimidine, 2-1, (0.1 g, 0.908 mmol) was dissolved in DMF and then sodium hydride (0.036 g of a 60% dispersion, 0.908 mmol) was added and stirred for 15 minutes at 25 C. and then 2-chloro-1,3-thiazole-5-carbonitrile, 2-2, (0.131 g, 0.908 mmol) was added. This was heated at 100 C. for 2 hours. After this time the reaction was diluted with 4 mL of methanol and loaded onto a C18 prep lc column. The product, 2-3, was isolated via lyophilization from dioxane. 1H-NMR (DMSO): 8.42 ppm (s, 1H); 8.10 ppm (d, 1H); 6.45 ppm (d, 1H). 4,6-diaminopyrimidine hemisulfate, hemisulfate of 3-1, (0.10 g, 0.314 mmol) and diisopropylethylamine (0.122 g, 0.942 mmol) were suspended in n-butanol (1 mL) and then solid 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.091 g, 0.628 mmol) was added and heated at 125 C. for 18 hours. The product 3-2 was purified on C18 preparative hplc and the product was isolated upon evaporation. Hi-Res MS: calc: 219.0448 found: 219.0448. 1H-NMR (DMSO): 8.36 ppm (s, 1H); 8.26 ppm (s, 1H); 7.20 ppm (s, 1H); 6.12 pm (s, 1H).

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 156-81-0, Pyrimidine-2,4-diamine.

Reference:
Patent; Bilodeau, Mark T.; Hartman, George D.; Hoffman JR., Jacob M.; Sisko, John T.; Manley, Peter J.; Smith, Anthony M.; Tucker, Thomas J.; Lumma JR., William C.; Rodman, Leonard; US2002/137755; (2002); A1;,
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932-52-5, Adding a certain compound to certain chemical reactions, such as: 932-52-5, 5-Aminopyrimidine-2,4(1H,3H)-dione, 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, 932-52-5, blongs to pyrimidines compound.

General procedure: A suspension of 5-aminouracil 1 (1 mmol) in dry pyridine (7.5 mL) was cooled to 0 C and the appropriate sulfonyl chloride (1 mmol) was added. The reaction mixture was stirred at room temperature until the TLC showed the reaction was completed (1.5-20 h). The solvent was removed under reduced pressure and the crude product was recrystallized from methanol or aqueous methanol to afford the product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,932-52-5, its application will become more common.

Reference:
Article; Ismaili, Hamit; Ban, ?eljka; Mati?, Josipa; Safti?, Dijana; Juki?, Marijana; Glava?-Obrovac, Ljubica; ?ini?, Biserka; Croatica Chemica Acta; vol. 92; 2; (2019); p. 269 – 277;,
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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 59989-18-3 as follows., 59989-18-3

under protection of argon, the cuprous iodide (0.02 mmol, 3.8 mg), four-triphenylphosphine palladium (0.02 mmol, 23 mg) and 1 – octane, 5 – ethynyl uracil (0.4 mmol, 99.6 mg) are added to the 4, 4 – di (3, 4, 5 – c (dodecyl) benzyl alkyne base) – 2, 6 – diiodosalicylic -8 – (3, 4, 5 – c (dodecyl) phenyl) beryllium two pyrrole in (0.2 mmol, 480 mg). For syringe triethylamine (5 ml) is injected into the mixture and, in the 70 C reaction in oil bath for four hours. Thin layer chromatographic detection, to be the reaction is complete, the reaction also adding 20 ml water quenching reaction. Ethyl ether (3 ¡Á 40 ml) extraction product, organic phase water (3 ¡Á 40 ml) washing three times. Anhydrous magnesium sulfate drying, pressure reducing and steaming and in addition to the solvent. The crude product column chromatographic separation and purification, showering liquid to dichloromethane: ethyl acetate=50:1, volume ratio. The product methanol recrystallization is purple solid, 179.5 mg, yield is 68%.

The chemical industry reduces the impact on the environment during synthesis 59989-18-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Tianjin University; Chen Zhijian; Liu Ping; (17 pag.)CN107056829; (2017); A;,
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720-01-4, 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.720-01-4, name is Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate, molecular formula is C8H6ClF3N2O2, molecular weight is 254.59, as common compound, the synthetic route is as follows.

To a solution of ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate(30.2 g, 1 19.0 mmol) in ethanol (594 mL) under nitrogen were added palladium (10% on carbon, 50% water wet; 2.58g, 1.21 mmol) and diisopropylethylamine (50.0 mL, 286.0 mmol). The mixture stirred68 under hydrogen (1 atm). After 6 h, the mixture was filtered with Celite. The filtrate was concentrated and ethyl acetate was added. The mixture was washed with sat. NaHCO3 (2x), brine, dried over Na2SO4, filtered and concentrated to give the title compound (25.6 g). MS 221.1 (M+l ).

Statistics shows that 720-01-4 is playing an increasingly important role. we look forward to future research findings about Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BURGEY, Christopher, S.; DENG, Zhengwu, J.; NGUYEN, Diem, N.; PAONE, Daniel, V.; POTTEIGER, Craig, M.; STAUFFER, Shaun, R.; SEGERDELL, Carolyn; NOMLAND, Ashley; LIM, John, J.; WO2010/111058; (2010); A1;,
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56-09-7, 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 56-09-7, name is 2-Amino-6-hydroxypyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Palladium catalysts 31a-c, 103, 104 and 105 were synthesized following reported procedures.20,24 2-amino-4,6-dihydroxypyrimidine or pyrimidine-4,6-diol based ligands (95 and 97) (20.0 mumol) weredissolved in an aqueous solution of YOH (0.4 mL, 0.1m) in an ultrasonic bath for 2 minutes. Thepalladium source (10.0 mumol) was added and the mixture was magnetically stirred at 65 C for 30 minutes, deionized water (0.6 mL) was then added to afford a 10.0 mM catalyst solutions of 31a-c and,103-105. The 40.0 mM catalyst solution was achieved with a 0.2 M solution of YOH.

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 56-09-7, 2-Amino-6-hydroxypyrimidin-4(3H)-one.

Reference:
Article; Tessier, Romain; Ceballos, Javier; Guidotti, Nora; Simonet-Davin, Raphael; Fierz, Beat; Waser, Jerome; Chem; vol. 5; 8; (2019); p. 2243 – 2263;,
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302964-08-5 , The common heterocyclic compound, 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, molecular formula is C16H13Cl2N5OS, 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.

Example 9; Procedure for the Preparation of Dasatinib Form EA mixture of compound 1 (0.30 g, 0.76 mmol), N-(2-hydroxyethyl)piperazine (0.52 g, 3.99 mmol) and N-ethyldiisopropylamine (0.26 ml, 1.52 mmol) in 2-methyl-THF (1.0 ml) was refluxed for 3 hours. The solution was slowly cooled to 0-5 C. Product was filtered off and washed with 2-methyl-THF and dried on the filter. Yield: 0.45 g.

According to the analysis of related databases, 302964-08-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIMO, Ondrej; Filipcik, Jiri; Martaus, Alexandr; Jegorov, Alexandr; Gavenda, Ales; Aronhime, Judith; Vraspir, Pavel; Koltai, Tamas; Faustmann, Jiri; Gabriel, Roman; US2009/118297; (2009); A1;,
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4595-59-9, 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. 4595-59-9, name is 5-Bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: K3PO4 (531 mg, 2.5 mmol) was added to a solution of 5-bromopyrimidine (1) (159 mg, 1.0 mmol), 2-thienylboronic acid(2) [3-thienylboronic acid (3), benzo[b]thien-2-ylboronic acid (4) orbenzo[b]thien-3-ylboronic acid (5)] (1.5 mmol) and trans-bis(dicyclohexylamine)palladium(II) acetate (29 mg, 0.05 mmol) in EtOH(10 mL). The resulting suspension was stirred at ambient temperaturefor 24 h. EtOH was evaporated under reduced pressure andthe residue was suspended in CH2Cl2 (20 mL) and filtered frominorganic salts. After that solvent was distilled off under reducedpressure, and the residue was purified by flash column chromatographyon silica gel (hexane/ethyl acetate, 1:3) to afford thedesired cross-coupling products (6, 7, 8 or 9).

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 4595-59-9, 5-Bromopyrimidine.

Reference:
Article; Verbitskiy, Egor V.; Cheprakova, Ekaterina M.; Slepukhin, Pavel A.; Kravchenko, Marionella A.; Skornyakov, Sergey N.; Rusinov, Gennady L.; Chupakhin, Oleg N.; Charushin, Valery N.; European Journal of Medicinal Chemistry; vol. 97; (2015); p. 225 – 234;,
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