Pyrimidines

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. 938443-20-0, name is 2,4,7-Trichloropyrido[2,3-d]pyrimidine, molecular formula is C7H2Cl3N3, 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. Application In Synthesis of 2,4,7-Trichloropyrido[2,3-d]pyrimidine

To a solution of 2,4,7-trichloropyrido[2,3-d]pyrimidine (4.0 g, 17.06 mmol, 1.0 equiv) in DMA (10 mL) was added (3S)-3-methylmorpholine (4.31 g, 42.65 mmol, 2.5 equiv) and DIPEA (5.51 g, 42.65 mmol, 7.43 mL, 2.5 equiv). The reaction solution was heated to 70 C for 48 h. The reaction suspension was cooled to room temperature, poured into cold H2O (50 mL) to precipitate out a solid. The solid was filtered and the filter cake was rinsed with H2O, and dried under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (0100% petroleum ether/EtOAc) to give (3S)-4-[7- chloro-2-[(3S)-3-methylmorpholin-4-yl]pyrido[2,3-d] pyrimidin-4-yl] 3-methyl-morpholine (3.5 g, 56.4% yield) as a yellow solid. LCMS (ESI) m/z: [M + H] calcd for C17H22ClN5O2: 364.15; found 364.2

With the rapid development of chemical substances, we look forward to future research findings about 938443-20-0.

Reference:
Patent; REVOLUTION MEDICINES, INC.; PITZEN, Jennifer; GLIEDT, Micah James Evans; BURNETT, G. Leslie; AGGEN, James Bradley; KISS, Gert; CREGG, James Joseph; SEMKO, Christopher Michael; WON, Walter; WANG, Gang; LEE, Julie Chu-Li; THOTTUMKARA, Arun P.; GILL, Adrian Liam; MELLEM, Kevin T.; (484 pag.)WO2019/212990; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3764-01-0, 2,4,6-Trichloropyrimidine, 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, 3764-01-0, blongs to pyrimidines compound. Formula: C4HCl3N2

Take 5000ml three necked flask, equipped with mechanical stirrer, condenser. Feed: 18.2 g of 2,4,6-trichloropyrimidine (molecular weight 182,0.10 mol), phenylboronic acid 28.1 g (molecular weight 122,0.23 mol), tetrakis(triphenylphosphine)palladium 12.0g (0.0104mol), potassium carbonate 60 g (0.435 mol), tetrahydrofuran 600 ml, toluene 400 ml, water 400 ml. Mechanical agitation was initiated under conditions of reduced pressure ventilation Ar gas three times to maintain protection, monitoring the reaction by TLC (thin layer chromatography), refluxed for 8 hours, the reaction was complete. Allowed to cool, the reaction system was divided into two layers, the organic layer was separated and evaporated to dryness to give a solid product, which was recrystallized from toluene to give intermediate M3-1 was 19.9 g, molecular weight 266, 75% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3764-01-0, its application will become more common.

Reference:
Patent; Kunshan Visionox Display Technology?Co., Ltd; Tsinghua University; Beijing Visionox Technology Co. Ltdk; QIU, YONG; TANG, JINMING; FAN, HONGTAO; DUAN, LIAN; REN, XUEYAN; (97 pag.)CN103664906; (2016); B;,
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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 111196-81-7, name is 2-Chloro-5-ethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Chloro-5-ethylpyrimidine

General procedure: Add in the reaction bottleBoc-based disubstituted pyrimidopyrimidine (50 mg, 0.09 mmol),2-chloro-5-ethylpyrimidine (18 mg, 0.13 mmol),TEA (27 mg, 0.45 mmol) and DCM (2 mL).The reaction was stirred at room temperature overnight, and the reaction mixture was diluted with dichloromethane.The organic phase was washed with brine, dried over anhydrous sodiumThe crude product using silica gel column chromatography (petroleum ether: ethyl acetate = 1: 1) to give a pale yellow solid, yield 45% reaction.

With the rapid development of chemical substances, we look forward to future research findings about 111196-81-7.

Reference:
Patent; Jiangxi University of Traditional Chinese Medicine; Yang Zunhua; Fang Yuanying; Liu Ronghua; He Mingzhen; Wang Qi; Li Zhifeng; (13 pag.)CN109761990; (2019); A;,
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Related Products of 4983-28-2 ,Some common heterocyclic compound, 4983-28-2, molecular formula is C4H3ClN2O, 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.

2-Chloropyrimidin-5-ol (13.0 g, 100 mmol) was dissolved in DMF (130 mL) (solution) and K2C03 (27.5 g, 199 mmol) was added (suspension), followed by iodoethane (16.1 mL, 199 mmol). The reaction mixture was stirred at 50¡ãC for 4 hr and subsequently cooled to ambient temperature and stirred overnight. The reaction mixture was partitioned between EtOAc (650 mL) and 10percent aqueous NaCl (650 mL). The organic layer was washed with 10percent aqueous NaCl (650 mL). The first aqueous layer was extracted with EtOAc (325 mL). The combined organic layers-were driedOver Na2S0 , filtered, and concentrated in vacuo. The crude mixture was diluted with D’CM-to a final volume of 40 mL and purified by flash chromatography (MPLC, 5-4percent EtOAc-Hexanes) to provide 2-chloro-5-ethoxypyrimidine as a white solid.LRMS (EST) calc’d fbr C6K8C1N02 [M+H]+: 159; Found: 159

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4983-28-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; YOUNG, Jonathan; CZAKO, Barbara; ALTMAN, Michael; GUERIN, David; MARTINEZ, Michelle; RIVKIN, Alexey; WILSON, Kevin; LIPFORD, Kathryn; WHITE, Catherine; SURDI, Laura; CHICHETTI, Stephanie; DANIELS, Matthew, H.; AHEARN, Sean, P.; FALCONE, Danielle; OSIMBONI, Ekundayo; WO2011/84402; (2011); 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. 89487-99-0, name is 4-Hydroxy-2-(methylthio)pyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below., name: 4-Hydroxy-2-(methylthio)pyrimidine-5-carbonitrile

Step B: A mixture of 4-hydroxy-2-methylsulfanyl-pyrimidine-5-carbonitrile (2.76 g) and phosphorus oxychloride (15 mL) was heated at reflux, under argon atmosphere, for 3 h. The reaction mixture was cooled and then evaporated under reduced pressure. Hexane was added to the residue and the mixture was heated at reflux, the resulting mixture was decanted and the same procedure was repeated for 4 times. The combined supernatant layers were evaporated to afford 1.13 g of 4-chloro-2-methylsulfanyl-pyrimidine-5-carbonitrile as a white powder.

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, 89487-99-0, 4-Hydroxy-2-(methylthio)pyrimidine-5-carbonitrile.

Reference:
Patent; Roche Palo Alto LLC; US2009/270389; (2009); A1;,
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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. 22536-63-6, name is 2-Chloro-4-methoxypyrimidine, molecular formula is C5H5ClN2O, 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. Product Details of 22536-63-6

Reference Example 8 2-(4-Iodophenoxy)-4-methoxypyrimidine [Show Image] Under an argon atmosphere, sodium hydride (108 mg) was added to a solution of 4-iodophenol (220 mg) and 2-chloro-4-methoxypyrimidine (168 mg) in anhydrous DMF (10 ml), and the resulting mixture was stirred at 125C for 9 hours. The reaction solution was cooled to room temperature and water was added thereto, followed by extracting the resulting mixture with ethyl acetate. Organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate = 5/1) to obtain 2-(4-iodophenoxy)-4-methoxypyrimidine (312 mg).

With the rapid development of chemical substances, we look forward to future research findings about 22536-63-6.

Reference:
Patent; Toray Industries, Inc.; EP2033637; (2009); A1;; ; Patent; Toray Industries, Inc.; EP2042171; (2009); 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. 3435-28-7, name is 6-Methylpyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 3435-28-7

Step 5 : [2-(2,6-Dichloro-4-fluorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)amine A suspension of 4-chloro-2-(2,6-dichloro-4-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine (70 mg, 0.22 mmol), 6-methylpyrimidin-4-ylamine (26 mg, 0.24 mmol), Pd2(dba)3 (10 mg, 0.011 mmol), Xantphos (12.8 mg, 0.022 mmol) and cesium carbonate (144 mg, 0.44 mmol) in dioxane (3 ml) was sealed in a microwave vial, purged with nitrogen and irradiated at 150 C for 25 minutes in the microwave. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resultant residue was purified by silica gel flash chromatography (50-100% ethyl acetate in cyclohexane), then further triturated with diethyl ether :pentane (1 : 1) to afford the title compound as a yellow solid (53 mg, 62% yield). ? NMR (400 MHz, DMSO-dg): d 10.65 (br s, 1H), 9.15 (s, 1H), 8.70 (s, 1H), 8.51 (s, 1H), 8.00 (d, J = 6.4 Hz, 1H), 7.93 (d, J = 8.4 Hz, 2H), 7.23 (d, J = 6.4 Hz, 1H), 2.46 (s, 3H). LCMS (Method B): RT = 2.94 min, m/z: 389 [M+H+].

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, 3435-28-7, 6-Methylpyrimidin-4-amine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; GOODACRE, Simon; LAI, Yingjie; LIANG, Yun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/66061; (2012); A1;,
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Reference of 3029-64-9, Adding some certain compound to certain chemical reactions, such as: 3029-64-9, name is 2,4,6-Trichloro-5-cyanopyrimidine,molecular formula is C5Cl3N3, 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 3029-64-9.

b 4-Chloro-2,6-bis-cyclopropylamino-pyrimidine-5-carbonitrile To a solution of 500 mg (2.4 mmol) of 2,4,6-trichloro-5-cyano-pyrimidine in 30 ml of dioxane were added at room temperature 0.84 ml (4.8 mmol) of N-ethyl-diisopropylamine and 0.52 ml (7.2 mmol) of cyclopropylamine. The yellow reaction mixture was stirred at room temperature during 18 hours, then, for working-up, it was evaporated under reduced pressure. The residue obtained was then chromatographed on silica gel using a 3:1 mixture of dichloromethane and hexane as the eluent yielding 328 mg (1.3 mmol, 55percent of theory) of 4-chloro-2,6-bis-cyclopropylamino-pyrimidine-5-carbonitrile as a yellow solid; MS: [M+H]+=249.

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. 3029-64-9, 2,4,6-Trichloro-5-cyanopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Binggeli, Alfred; Maerki, Hans-Peter; Masquelin, Thierry; Mutel, Vincent; Wilhelm, Maurice; Wostl, Wolfgang; US2003/60466; (2003); A1;,
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Reference of 67434-65-5 ,Some common heterocyclic compound, 67434-65-5, molecular formula is C6H7ClN2, 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.

[0543] Procedure: To a stirred solution of 4-(sulfamoylamino)piperidin-1-ium chloride (0.10 g, 0.49 mmol) and 4-chloro-5,6-dimethylpyrimidine (0.06 g, 0.41mmol) in dimethyl formamide (4 mL)was added potassium carbonate (0.17 g, 1.24 mmol) and heated the reaction mixture to 90 C for 16 h. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with water (20 mL), extracted with dichloromethane (2 x 40mL). The combined organic layer ware washed with brine (20mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain crude compound. The crude residue was purified by prep-HPLC. Column: Intersil ODS 3V (250mmx4.6mmx5mic), Mobile phase (A): 0.1% TFA in water, Mobile phase(B): ACN, Flow rate: 1.0 mL/min to afford N-(1-(5,6-dimethylpyrimidin-4-yl)piperidin-4-yl)sulfamide (0.03 g, 14%) as white solid.1HNMR (400 MHz, DMSO-d6): delta 8.37 (s, 1H), 6.59 (d, J = 7.2 Hz, 1H), 6.46 (s, 2H), 3.58-3.62 (m, 2H), 3.27 (s, 1H), 2.84 (t, J = 11.2 Hz, 2H), 2.30 (s, 3H), 2.07 (s, 3H), 1.92-1.95 (m, 2H), 1.46-1.55 (m, 2H). LC-MS (ES) m/z = 286.2 [M+H]+. HPLC purity: 99.9 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67434-65-5, its application will become more common.

Reference:
Patent; MAVUPHARMA, INC.; GALLATIN, William Michael; ODINGO, Joshua; DIETSCH, Gregory N.; FLORIO, Vincent; VENKATESHAPPA, Chandregowda; DURAISWAMY, Athisayamani Jeyaraj; (273 pag.)WO2019/46778; (2019); A1;,
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Synthetic Route of 876343-10-1, Adding some certain compound to certain chemical reactions, such as: 876343-10-1, name is 4-Chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H3ClIN3, 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 876343-10-1.

A mixture of 4-chloro-6-iodo- 7/-/-pyrrolo[2,3-c]pyrimidine (400 mg, 1.43 mmol), phenylboronic acid (524 mg, 4.29 mmol), copper(ll) acetate (520 mg, 2.86 mmol) and 1 , 10-phenanthroline (516 mg, 2.86 mmol) in anhydrous dimethylformamide (16 mL) was stirred for 16 h. The reaction mixture was partitioned between saturated ammonium chloride (80 mL), water (80 mL) and ethyl acetate (80 mL). The separated aqueous phase was extracted with ethyl acetate (3 x 80 mL). The combined organic phase was washed with 1 : 1 brine/water (4 x 80 mL), dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (0- 30% EtOAc in cyclohexane) to afford the title compound (207 mg, 41 %). LCMS (Method B): RT = 1.42 min, m/z = 356 [M+H]+.

According to the analysis of related databases, 876343-10-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMAC DISCOVERY LIMITED; O’DOWD, Colin; HARRISON, Tim; HEWITT, Peter; ROUNTREE, Shane; HUGUES, Miel; BURKAMP, Frank; JORDAN, Linda; HELM, Matthew; BROCCATELLI, Fabio; CRAWFORD, James John; GAZZARD, Lewis; WERTZ, Ingrid; LEE, Wendy; (304 pag.)WO2018/73602; (2018); A1;,
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