Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 5750-76-5, 2,4,5-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, 5750-76-5, blongs to pyrimidines compound. Computed Properties of C4HCl3N2

To a 250 mL round bottom flask equipped with a stir bar was added 1 g 5-chloro- 2,4-dichloro- pyrimidine, and l5mL of diethyl ether. The mixture was cooled to 0C inan ice bath and then 1 equivalent of sodium methoxide in methanol (prepared from reacting 120 mg of sodium with 4 mL of methanol at room temperature) was slowly added. The reaction was stirred over night at room temperature and checked by LCMS. The white precipitate was filtered and the solid washed with cold methanol. After drying, 0.98 g of pure 2,5-dichloro-4-methoxypyrimidine was obtained and this material wasused without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5750-76-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAKER-GLENN, Charles; CHAMBERS, Mark; CHAN, Bryan K.; ESTRADA, Anthony; SWEENEY, Zachary Kevin; WO2013/79495; (2013); A1;,
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Reference of 955368-90-8 , The common heterocyclic compound, 955368-90-8, name is 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, molecular formula is C9H10N4OS, 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.

Into a 25 mL microwave vial was added 2-allyl-6-(methylthio)-1H-pyrazolo[3,4- d]pyrimidin-3(2H)-one (275 mg, 1.235 mmol) (obtained according to EP2213673B1, Production Example 1, p37), [(5-bromopyridin-3-yl)imino]dimethyl-A6-sulfanon (400 mg, 1.61 mmol), potassium carbonate (239 mg, 1.73 mmol) and dioxane (5 mL). The resultant suspension was degassed (bubbling of N2) and copper (I) iodide (235 mg, 1.235 mmol) was added followed by N1,N2-dimethylethane-1,2-diamine (0.133 mL,1.24 mmol). The vial was capped and the reaction mixture was stirred at 95 00 overnight. After cooling to RT the reaction mixture was transferred to a separation funnel, NH4OH (aq, 20 mL) was added and the resulting mixture was extracted with EtOAc (3 x 30 mL). The organic phases were combined, dried and evaporated under vacuum. The residue was purified using flash chromatography (0-15% MeOH in EtOAc). The product containing fractions were concentrated to give the title compound (60 mg, 12.44 % yield) as an yellowish oil that solidified upon storage. LCMS (Method C): RT = 0.99 mi mlz = 391 [M+H].1H NMR (300 MHz, ODd3) O 9.21 (5, 1H), 8.64 (5, 1H), 8.57 (5, 1H), 8.12 (5, 1H),5.70-5.41 (m, 1H), 5.17 (t, J = 5.1 Hz, 1H), 4.96 (d, J = 17.0 Hz, 2H), 4.53 (d, J = 6.0 Hz, 2H), 3.31 (5, 6H), 2.53 (5, 3H)

The synthetic route of 955368-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BURKAMP, Frank; ROUNTREE, James Samuel Shane; TREDER, Adam Piotr; (155 pag.)WO2018/11569; (2018); A1;,
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Reference of 63558-65-6, Adding some certain compound to certain chemical reactions, such as: 63558-65-6, name is 4-Chloro-5-iodopyrimidine,molecular formula is C4H2ClIN2, 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 63558-65-6.

Preparation 57A: 5-Iodo-4-(2H-l,2, -triazol-2-yl)pyrimidine[00244] To a solution of lH-l,2,3-triazole (63.2 mg, 0.915 mmol) in THF (Volume: 241 1 ??), was added portion wise at 0 C, NaH (39.9 mg, 0.998 mmol). The reaction mixture was stirred at that temperature for 30 min, then 4-chloro-5-iodopyrimidine (200 mg, 0.832 mmol) was added. The reaction mixture was allowed to warm to room temperature. To this solution was added saturated aqueous NH4C1 and the mixture was allowed to stir for 5 min at which time it was diluted with ethyl acetate and extracted 2X. The combined organics were washed with brine IX. The organics were dried overNa2S04, filtered and concentrated in vacuo to afford the title compound (90 mg, 40%).

According to the analysis of related databases, 63558-65-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; VELAPARTHI, Upender; LIU, Peiying; WO2013/49263; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3177-20-6, Methyl 2,4-dichloropyrimidine-5-carboxylate, 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, COA of Formula: C6H4Cl2N2O2, blongs to pyrimidines compound. COA of Formula: C6H4Cl2N2O2

To a solution of 2,4-dichloropyrimidine-5-carbonyl chloride (500 mg, 2.38 mmol) in dichloromethane (30 mL) was added methanol (87.6 mg, 2.73 mmol) and diisopropylethylamine (369 mg, 2.86 mmol) at 0 ¡ãC. The resulting mixture was stirred for at 0 ¡ãC 1 h. Then the solvent was removed. The residue (412mg, 2.0 mmol) was dissolved in IPA (20 mL) followed by the addition of Z-Ormthine (465 mg, 2.0 mmol) and N,N- diisopropylethylamine (388 mg, 3.0 mmol). The resulting mixture was stirred at 0 ¡ãC for 90 min, then dichloromethane (5.0 mL) was added. The resulting mixture was stirred at 0 ¡ãC for 1.0 h and at room temperature overnight. Solvent was removed and the residue (MS m/z 403.30 [M+H]+) was dissolved in DMF (5.0 mL) and was added dropwise into a solution of 1,4-diaminobutane (1.68g, 19.1 mmol) in DMF (1.0 mL) at room temperature. The resulting mixture was heated to 45 ¡ãC for l . The solvent was removed and the residue was dissolved in ethyl acetate (35 mL) and washed with water (3x). The organic layer was dried ( a2S04), filtered and concentrated. The residue was purified on HPLC to provide (S)-5-((2-((4- aminobutyl)amino)-5-(methoxycarbonyl)pyrimidin-4-yl)amino)-2-((tert-butoxycarbonyl) amino)pentanoic acid as a semisolid (MS m/z 455.30 [M+H]+). The semisolid (595 mg, 1.31 mmol) was dissolved in DMF (150 mL), then TBTU (546.4 mg, 1.70 mmol) and DIEA (508 mg, 3.93 mmol) were added sequentially. The resulting mixture was stirred at room temperature overnight. The solvent was removed. The residue was dissolved in ethyl acetate and washed with water (3x). The organic layer was dried (Na2S04), filtered and concentrated. The residue was purified on HPLC to provide the totle compound (UNC2343A). 1H NM (400 MHz, CD3OD) S 8.42 (s, 1H), 4.08-3.99 (m, 1H), 3.90-3.84 (m, 3H), 3.59-3.47 (m, 2H), 3.46-3.31 (m, 2H), 3.28-3.21 (m, 1H), 3.09-2.95 (m, 1H), 1.90-1.52 (m, 8H), 1.51- 1.32 (m, 9H); MS m/z 437.30 [M+H]+.

The synthetic route of 3177-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WANG, Xiaodong; ZHANG, Weihe; FRYE, Stephen; WO2015/157127; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 25940-35-6, Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, 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, Safety of Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, blongs to pyrimidines compound. Safety of Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

To the mixture of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (42 mg, 0.26 mmol) and diisopropylethylamine (0.09 mL, 0.52 mmol) in DMF (2 mL) was added 2-(7-aza-1H- benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (131 mg, 0.34 mmol) then the mixture was stirred at 25 oC for 15 min. To the mixture was added a solution of 2-[4-(5- amino-2,2-dimethyl-3H-benzofuran-6-yl)piperazin-1-yl]ethanol (50 mg, 0.17 mmol) in DMF (2 mL) and the resulting mixture was stirred at 25 oC for 16h. The mixture was purified by preparative HPLC(Xbridge 21.2*250 mm c18, 10um, A: acetonitrile 10-70%; B:10 mM ammonium bicarbonate in water) to afford N-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2,2- dimethyl-3H-benzofuran-5-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (45 mg, 60%) as a yellow solid.1H NMR (400 MHz,DMSO-d6) delta 10.42(s, 1H), 9.37(dd, J = 1.6 , 7.2Hz, 1H), 8.92 (dd, J = 1.6, 4.4Hz, 1H), 8.68(s, 1H), 8.31(s, 1H), 7.36(dd, J = 4.4,7.2Hz, 1H), 6.69(s, 1H), 4.45(t, J =5.2Hz, 1H), 3.54(q, J = 5.6 Hz, 2H), 3.00(s, 2H), 2.84-2.78(m, 4H), 2.74-2.61 (m, 4H), 2.50(t, J = 5.6 Hz ,2H), 1.41(s, 6H). MS (ESI): m/z = 437.3 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,25940-35-6, Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian, C.; GOBBI, Alberto; KIEFER, James, Richard, Jr.; KOLESNIKOV, Aleksandr; OLIVERO, Alan, G.; DROBNICK, Joy; LIANG, Jun; RAJAPAKSA, Naomi; (846 pag.)WO2017/108723; (2017); A2;,
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Synthetic Route of 153435-63-3, 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 153435-63-3, name is 2-(Tributylstannyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 3-8 (Trans)-8-[(2,5′-bipyrimidin-2′-Vlamino)methyl]-3-(2-pyridinyl)-1-oxa-3-azaspiro[4.5]decan-2-one To a solution of (trans)-8-{[(5-bromo-2-pyrimidinyl)amino]methyl}-3-(2-pyridinyl)-1-oxa-3-azaspiro[4.5]decan-2-one (Intermediate 24, 30 mg, 0.072 mmol) in dimethylsulfoxide (3 ml) 2-(tributylstannanyl)pyrimidine (26.5 mg, 0.072 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.32 mg, 2.87 mumol) were added and the resulting mixture was irradiated in a microwave oven at 120 C. for 10 min. The crude solution was first eluted on a SCX cartridge (DCM/MeOH/NH3 (2M soln in MeOH) 100/0/0 to 80/10/10) and evaporated to dryness. Purification by silica gel chromatography (SP1 automated instrument, SNAP 10 g Si cartridge, elution in gradient with 0%-10% MeOHDCM) gave the title compound as a white solid (15 mg, 0.036 mmol, 50%).

According to the analysis of related databases, 153435-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Biagetti, Matteo; Contini, Stefania Anna; Genski, Thorsten; Guery, Sebastien; Leslie, Colin Philip; Mazzali, Angelica; Pizzi, Domenica Antonia; Sabbatini, Fabio Maria; Seri, Catia; US2009/203705; (2009); 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. 1189169-37-6, name is 1-(5-Bromopyrimidin-2-yl)ethanone. A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(5-Bromopyrimidin-2-yl)ethanone

E. 6-(5-bromopyrimidin-2-yl)pyridazin-3(2H)-one To a 50 mL 1 neck flask equipped with magnetic stirrer, nitrogen inlet and thermometer was charged 0.22 grams (g) of 1-(5-bromopyrimidin-2-yl)ethanone (1.09 mmol), 0.17 g (1.1 mmol) glyoxylic acid, and 2.5 mL of methanol and 2.5 mls of water. To this solution was added 0.3 g (2.2 mmol) of potassium carbonate. The reaction was stirred overnight at room temperature. Methanol was then concentrated under vacuum on a rotary evaporator, and the resulting aqueous solution was washed twice with 5 mls of methylene chloride. To the aqueous solution was then added 0.6 mls of acetic acid and 0.07 g (1.4 mmol) of hydrazine monohydrate. This solution was refluxed for 2 hours, then cooled at 5 C. The resulting solid was collected by vacuum filtration to afford 30 mg of a brown solid which was consistent with the target compound upon analysis by NMR. The NMR data is as follows: 300 MHz 1H NMR (CDCl3, TMS=0 ppm) 2.75 (s, 3H); 9.00 (s 2H).

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, 1189169-37-6, 1-(5-Bromopyrimidin-2-yl)ethanone.

Reference:
Patent; DOW AGROSCIENCES LLC; US2009/253708; (2009); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 873-83-6 ,Some common heterocyclic compound, 873-83-6, molecular formula is C4H5N3O2, 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.

General procedure: A mixture of 4-aminocoumarin /6-aminouracil (1.0 mmol), isatin/5-bromoisatin (1.0 mmol), 1,3-diketo compound (cyclohexane-1,3-dione, indane-1,3-dione, dimedone, 1,3-dimethylbarbituric acid)(1.0 mmol) and PEG?OSO3H (15 molpercent) was taken in 5 ml water. The mixture was stirred at 70 oC for a required period of time (TLC). After completion of each reaction, the crude product (insoluble in water) was filtered and it was washed with ethanol. The isolated product was recrystallized from DMF?water to get the pure product.#10;#10;#10;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,873-83-6, its application will become more common.

Reference:
Article; Paul, Sanjay; Das, Asish R.; Tetrahedron Letters; vol. 54; 9; (2013); p. 1149 – 1154;,
Pyrimidine | C4H4N2 – PubChem,
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Synthetic Route of 1722-12-9, Adding some certain compound to certain chemical reactions, such as: 1722-12-9, name is 2-Chloropyrimidine,molecular formula is C4H3ClN2, 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 1722-12-9.

Under N2, 2-chloropyrimidine (200 g, 1.75 mol) was added in 5 portions to aqueous HI (850 ml, 57% in water) at -10 to -5 C. The mixture was stirred at -10 to -5 C. and the reaction was followed by HPLC. After complete reaction (60 to 120 min), the pH was set to 7.25+/-0.25 with NaOH (30%) and the temperature was increased to 18-23 C. To decolorize the mixture, 16 g Na2SO3 was added, decreasing the pH to 3+/-1. TBME (600 ml) was added to the mixture and the mixture was saturated with NaCl (300 g). The phases were separated and the aqueous phase was extracted with TBME (4¡Á400 ml). The combined organic layers were washed with aqueous Na2SO3 (50 ml) (1%) and water (100 ml). The organic layer was evaporated to dryness and co-evaporated with TBME (100 ml) under vacuum at 45 to 50 C. Yield: 330 g (90%). Assay (HPLC): 98% pure vs. standard.

According to the analysis of related databases, 1722-12-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mergelsberg, Ingrid; Werne, Gerald; US2006/58343; (2006); A1;,
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Synthetic Route of 156-81-0 , The common heterocyclic compound, 156-81-0, name is Pyrimidine-2,4-diamine, molecular formula is C4H6N4, 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-Bromo-l-(3-fluorophenyl)ethanone (10.9 g, 50 mmol) was added to a solution of 2,4- diaminopyrimidine (3.70 g, 34 mmol) in acetone (185 ml), and the mixture was heated to reflux for 6 h. The cooled suspension was filtered and the precipitate was washed with acetone (50 ml). The solid was re-suspended in water (35 ml) and NH40Haq. (25%, 50 ml), then it was collected over a glass fiber paper and the filtrate was washed with Iota?0 (75 ml). After drying under vacuum, the product was obtained (5.56 g, 72%) as a yellow solid.MS (m/z) = 229.1 [M+H+].

The synthetic route of 156-81-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALVAREZ SANCHEZ, Ruben; BLEICHER, Konrad; FLOHR, Alexander; GOBBI, Luca; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RUDOLPH, Markus; WO2011/117264; (2011); A1;,
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