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. 4595-61-3, name is Pyrimidine-5-carboxylic acid, molecular formula is C5H4N2O2, 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. Safety of Pyrimidine-5-carboxylic acid

Example 1.32: Preparation of (tf)-(5-(4-(2-(2-Methylpyrrolidin-l- yl)ethyl)phenyl)isoindolin-2-yl)(pyrimidin-5-yl)methanone (Compound 29).In a 10 mL microwave vial were placed (R)-5-(4-(2-(2-methylpyrrolidin-l- yl)ethyl)phenyl)isoindoline (0.100 g, 0.326 mmol), pyrimidine-5-carboxylic acid (0.0607 g, 0.489 mmol), triethylamine (0.0910 mL, 0.653 mmol), PS-carbodiimide (1.02 g, 1.63 mmol), and CH2Cl2 (3 mL). The reaction was heated under microwave irradiation at 1200C for 1 h. The mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by HPLC to give the TFA salt of the title compound as a white solid (0.060 mg). LCMS m/z = 413.2 [M+H]+; 1H NMR (400 MHz, Methanol-*/,) delta ppm 1.26-1.31 (m, 3H), 1.48 (dd, J = 6.44, 3.66 Hz, 4H), 2.10 (s, 2H), 3.03-3.18 (m, 2H), 3.44-3.58 (m, IH), 3.69-3.80 (fn, IH), 4.91-4.96 (m, IH), 4.96-5.00 (m, IH), 5.01-5.08 (m, 2H), 7.34-7.50 (m, 4H), 7.54-7.67 (m, 4H), 9.10 (s, 2H), 9.30 (s, IH).

With the rapid development of chemical substances, we look forward to future research findings about 4595-61-3.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/105206; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5604-46-6, 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, 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, Formula: C5H3Cl2N3O, blongs to pyrimidines compound. Formula: C5H3Cl2N3O

To a mixture of 112a (253 mg, 1.1 mmol) and 112b (192 mg, 1.0 mmol) was added DMF (20 ml) and the reaction mixture was stirred at room temperature overnight. Then poured the mixyure into ice/saturated sodium bicarbonate solution (40 ml). The precipitated solid was collected by filtration and washed with water. The solid was taken in DMF (10 ml) and added gl. acetic acid (10 drops). The reaction mixture was stirred at room temperature overnight and processed as above. The solid thus obtained (223 mg) was taken in dichloromethane (10 ml) and treated with DDQ (138 mg, 0.6 mmol) at room temperature for 1 hr. The reaction mixture was diluted with chloroform (30 ml) and washed with saturated sodium bicarbonate solution (50 ml). Separated the organic layer, and the aqueous layer was extracted with EtOAc (50 ml). Combined the organic layers, dried (Na2SO4), filtered and concentrated to provide 112c which was taken further without any purification.

The synthetic route of 5604-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; SOUTHERN RESEARCH INSTITUTE; ARASAPPAN, Ashok; NJOROGE, F., George; BENNETT, Frank; GIRIJAVALLABHAN, Vinay, M.; HUANG, Yuhua; HUELGAS, Regina; PIWINSKI, John, J.; SHIH, Neng-Yang; VERMA, Vishal; VELAZQUEZ, Francisco; VENKATRAMAN, Srikanth; KWONG, Cecil, D.; ANANTHAN, Subramaniam; CLARK, Jeremy; GENG, Feng; KEZAR, Hollis, S., III.; MADDRY, Joseph, A.; REYNOLDS, Robert, C.; ROYCHOWDHURY, Abhijit; SECRIST, John, A., III.; FOWLER, Anita, T.; WO2010/22121; (2010); A1;,
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Related Products of 10320-42-0, 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. 10320-42-0, name is 2-Chloro-5-nitropyrimidine, molecular formula is C4H2ClN3O2, 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.

Triethylamine (7.2 mL, 51.8 mmol) was added to a solution of piperazine-1-sulfonic acid dimethyl amide (10 g, 51.8 mmol) dissolved in 400 mL of THF. 2-chloro-5-nitropyrimidine (7.7 g, 48.3 mmol) dissolved in 20 mL of THF was added to the stirred mixture. After 24 hours stirring at room temperature (RT), THF was removed under vacuum and 600 mL of CHCl3 was added to the residue. The CHCl3 layer was washed with 0.5 N HCl and brine, dried over Na2SO4, and filtered. Solvent evaporation gave 14.1 g (92percent) of straw yellow solid 1-N,N’-dimethylsulfamoyl-4-(2-(5-nitropyrimidyl)piperazine. The structure was confirmed by 1H-NMR. 1H NMR (CDCl3) delta9.08 (s, 2H), 4.09 (appt, J=5.13 Hz, 4H), 3.35 (appt, J=5.13 Hz, 4H), 2.87 (s, 6H).

According to the analysis of related databases, 10320-42-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kador, Peter F.; Jin, Hongxia; US2009/105269; (2009); A1;,
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Synthetic Route of 18740-39-1, 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. 18740-39-1, name is 2,4-Dichlorothieno[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

Weigh 11-a (125 mg, 1 eq) and methyl p-aminobenzoate (67 mg, 1.2 eq). Butanol was added to dissolve, then p-toluenesulfonic acid (7 mg, 0.1 eq) was added, and the reaction was carried out at 170¡ã C. for 2 hours in the microwave. Cool and filter to obtain crude compound 12-a crude (168 mg, 99percent).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18740-39-1, 2,4-Dichlorothieno[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Xin Minxing; Tang Feng; Wen Jun; Shen Han; Tu Chongxing; Zhao Xinge; (48 pag.)CN104177363; (2018); B;,
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Related Products of 1500-85-2, 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. 1500-85-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H6N4, 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.

Scheme 3 NH2 NPhth XN phthalic anhydride XN N N DMAC N N H H 3-1 3-2 H H 3J. 32 To a 250 mL three-neck round bottom flask equipped with an overhead stirrer, nitrogen inlet, and thermocouple was charged 50 mL of dry N,N-dimethylacetamide followed by 5.0 g OF 7H-PYRROLO [2, 3-DLPYRIMIDIN-4-YLAMINE (U) [J. Davoll, J. Chem. SOC., 131-138 (1960)] and 11.6 g of phthalic anhydride. The resulting mixture was heated to 80 C for 8 h and then cooled to 10 C. Water (40 ML) was added while maintaining the temperature below 15 C. The resulting slurry was aged for 4 h, then filtered, and the filter washed with 20 ML of 1: 1 (v/v) dimethylacetamide/water followed by 30 ML of water. The cake was sucked dry, then washed with 50 ML of ethyl acetate. The solid was dried at 40 C under vacuum with a nitrogen sweep to give 8.1 g OF 4-PHTHALIMIDO-7H-PYRROLO [2, 3-d]pyrimidine (3-2); m. p. 276-277 C. LH NMR (DMSO-D6, 400 MHz) : 8 12. 14 (s, 1H), 8.79 (s, 1H), 8.01 (dd, J=5.5, 3.1 Hz, 2H), 7.92 (dd, J=5. 5,3. 1 HZ, 2H), 7.63 (dd, J=3.5, 2.4 Hz, 1H), 6.56 (dd, J=3.5, 1.8 Hz, 1H) ; 13C NMR (DMSO-D6, 100 MHZ) : 5 166.3, 154.2, 151.0, 145. 2,135. 7,132. 0,128. 7,124. 4,115. 2,100. 1.

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 1500-85-2, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine.

Reference:
Patent; MERCK & CO. INC.; WO2004/72090; (2004); A1;,
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Pyrimidine – Wikipedia

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. 23906-13-0, name is 2-Hydrazinyl-4,6-dimethylpyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 23906-13-0

A mixture of 2-hydrazinyl-4,6-dimethylpyrimidine (500 mg, 3.62 mmol) and 3- aminocrotononitrile (312 mg, 3.80 mmol) in ethanol (10 mL) was heated at reflux for 3 h and was then concentrated in vacuo. The crude product was recrystallized from methanol to afford 800 mg of l-(4,6-dimethylpyrimidin-2-yl)-3-methyl-lH-pyrazol-5-amine as a pale brown solid. Yield: 90%; m/z (ESI+) 226 (MNa+), 204 (MH+).

The synthetic route of 23906-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; TAIT, Bradley; POWELL, Noel, A.; CULLEN, Matthew; WO2012/154880; (2012); A1;,
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908240-50-6, 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. 908240-50-6, name is 2,4-Dichloropyrido[3,4-d]pyrimidine, molecular formula is C7H3Cl2N3, 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 the mixture of 2,4-dichloropyrido[3,4-d]pyrimidine (420.00 mg, 2.10 mmol) and 4-(l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazol-4-yl)aniline (408.70 mg, 1.68 mmol) in THF (10.00 mL) was added DIPEA (542.75 mg, 4.20 mmol, 733.45 uL). The mixture was stirred under N2 at 15 ¡ãC for 16 h. TLC (petroleum:EtOAc=0: l, Rf=0.40) showed one new main spot. The reaction mixture was diluted with water (30 mL) and the mixture was extracted with EtOAc (40 mLx3). The combined organic layers were washed dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by recrystallization (petroleum:EtOAc=10: l, 20 mL) to afford the title compound (620.00 mg, 72percent) as a yellow solid. 1H NMR (400 MHz, DMSO-i/6) delta 10.51 (s, 1H), 9.10 (s, 1H), 8.74 (d, J= 6.0 Hz, 1H), 8.45 (d, J= 5.6 Hz, 1H), 8.37 (s, 1H), 7.98 (s, 1H), 7.81 (d, J= 8.4 Hz, 2H), 7.71 (d, J = 8.8 Hz, 2H), 5.43-5.41 (m, 1H), 3.97-3.94 (m, 1H), 3.69-3.62 (m, 1H), 2.15-2.12 (m, 1H), 1.99- 1.94 (m, 2H), 1.72-1.65 (m, 1H), 1.57-1.56 (m, 2H).

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. 908240-50-6, 2,4-Dichloropyrido[3,4-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; KIM, Ji-In; POYUROVSKY, Masha; LIU, Kevin; BARSOTTI, Anthony; MORRIS, Koi; (344 pag.)WO2016/210330; (2016); A1;,
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1780-26-3, 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 1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To 12 ml of 1,4-dioxane, 0.75 g of phenylboronic acid, 1.67 g of potassium carbonate, 0.13 g of dichlorobis (triphenylphosphine) palladium and 1 g of 4,6- dichloro-2-methylpyrimidine were added. This mixture was stirred at 60C for 3 hours and then stirred at 800C for 6 hours. The reaction mixture was left standing to cool to room temperature, poured into an aqueous saturated ammonium chloride solution and then extracted three times with tert- butyl methyl ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to obtain 0.64 g of 4-chloro-2-methyl- 6-phenylpyrimidine.4-chloro-2-methyl-6-rhohenylpyrimidine 1 H-NMR : 2 . 78 ( s , 3H ) , 7 . 49-7 . 56 (m, 4H ) , 8 . 04 -8 . 07 (m, 2H )

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 1780-26-3, 2-Methyl-4,6-dichloropyrimidine.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; MIZUNO, Hajime; WO2010/134478; (2010); A1;,
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13479-88-4 ,Some common heterocyclic compound, 13479-88-4, molecular formula is C5HCl2N3S, 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.

Step 1 5-Chloro-N-(3,4,5-trimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine Procedure: To a stirred solution of 5,7-dichlorothiazolo[5,4-d]pyrimidine (200 mg, 0.97 mmol) and 3,4,5-trimethoxybenzenamine (230 mg, 1.25 mmol) in 7 mL of DMSO was added DIEA (188 mg, 1.45 mmol) in one portion at room temperature. Then the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into 40 mL of water, and the solid obtained was filtered, washed with water (10 mL) to give a crude product. It was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate) to give 5-chloro-N-(3,4,5-trimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (337 mg, 98.6%) as a yellow solid. LC-MS: 353.0 [M+H]+, 726.9 [2M+H]+, tR=1.56 min.

According to the analysis of related databases, 13479-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
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4983-28-2, 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. 4983-28-2, name is 2-Chloro-5-hydroxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (2R,5R)-tert-butyl 2-(hydroxymethyl)-5-methylmorpholine-4-carboxylate (1.2 g, 5.2 mmol) and 2-chloropyrimidin-5-ol (1 g, 7.5 mmol), DIAD(1.5 g 7.5 mmol) in THF (30 mL) was added triphenylphosphine (2 g, 7.5 mmol) at 0 ¡ãC, then the reaction was stirred at room temperature for 12 hours. The reaction solution was evaporated to dryness and the residue was purified by flash column chromatography, eluting with ethyl acetate: petroleum ether = 1:3 to afford the title compound (0.52 g, 1.52 mmol, 29 percent yield). LCMS Method D RT= 1.54 min, ES+ve 287.9 (M-tBu+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, 4983-28-2, 2-Chloro-5-hydroxypyrimidine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CASILLAS, Linda N.; HARLING, John David; MIAH, Afjal Hussain; SMITH, Ian Edward David; RACKHAM, Mark David; (204 pag.)WO2017/182418; (2017); A1;,
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