Day: March 15, 2021

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. 335654-06-3, name is 2-Chloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., category: pyrimidines

4-methoxy-7H-pyrrolo[2,3-d]pyrimidine (3) or 2-methoxy-7H-pyrrolo[2,3-d]pyrimidine (4) is prepared by reacting 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1) or 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (2), respectively, with sodium hydroxide in methanol as described by Girgis, N. et.al., J. Heterocyclic. Chem. 1989, 26:317-325.

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, 335654-06-3, 2-Chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Plexxikon, Inc.; US2009/286783; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 84905-80-6, 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.84905-80-6, name is 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

Example 171 Production of N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5-[2-(2-methoxyethoxy)ethyl]-5H-pyrrolo[3,2-d]pyrimidin-4-amine hydrochloride 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (500 mg) was dissolved in N,N-dimethylformamide (10 mL), and potassium carbonate (830 mg) and 2-(2-methoxyethoxy)ethyl 4-methylbenzenesulfonate (920 mg) were added and the mixture was stirred at room temperature for 12 hrs. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=50:50 ? 0:100). The obtained oil was dissolved in isopropyl alcohol (10 mL), and 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline was added. The mixture was stirred at 90C for 4 hrs, saturated aqueous sodium hydrogen carbonate was added to the reaction mixture under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated. The residue was separated and purified by silica gel column chromatography (eluent, ethyl acetate_methanol=100:0 ? ethyl acetate_methanol=90:10), and crystallized from 4N hydrochloric acid-ethyl acetate solution/hexane to give the title compound (277 mg). 1H-NMR(DMSO-d6) delta: 3.06 (3H, s), 3.33 – 3.35 (2H, m), 3.55 – 3.61 (2H, m), 3.83 – 3.86 (2H, m), 4.83 – 4.86 (2H, m), 6.71 (1H, d, J= 3 Hz), 7.24 – 7.72 (7H, m), 7.99 – 8.04 (2H, m), 8.77 (1H, s), 9.92 (1H, s).

Statistics shows that 84905-80-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1752457; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 659729-09-6, 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 659729-09-6, name is 4-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

1.27 g (4.92 mmol) of 4-chloro_6_ (4′-trifluoromethylphenyl) pyrimidine was weighed out,(0.85 g, 5.18 mmol) of trimethylbenzeneboronic acid,4 g of tetrakis (triphenylphosphine) palladium and 3 g of anhydrous sodium carbonate were placed in a 120 mL sealed tube,A mixture of tetrahydrofen sitan 30 mL and 20 mL of deionized water was placed in a sealed tube as a solvent, and a stirrer was added and the stopper was capped.The entire device vacuum nitrogen nitrogen replacement 3 ~ 4 times, placed in the oil bath pot,The mixture was heated to 115 C on a magnetic stirrer and refluxed for about 8 h.After the reaction,Sealed to cool to room temperature, the solution inside the sealed tube into the rotary bottle,The tetrahydrofuran solvent was distilled off under reduced pressure by rotary evaporator.The organic product was extracted with ethyl acetate and water for 3 to 4 times. The solvent was distilled off under reduced pressure. The spheroidized product was separated by petroleum ether: ethyl acetate 20: 1,To give a pale yellow solid, about 0.87 g, yield 51.6%.

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 659729-09-6, 4-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine.

Reference:
Patent; Anhui University of Technology; Tong Bihai; He Yuheng; Liu Yuanyuan; Jin Long; Zuo Dashuai; Wang Song; (25 pag.)CN106632488; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
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. 955368-90-8, name is 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one

Compound 1.1 (255 mg, 1 mmol),2-allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (222 mg, 1 mmol),Cuprous iodide (191 mg, 1 mmol),Anhydrous potassium carbonate (276 mg, 2 mmol)And N,N-dimethylethylenediamine (88 mg, 1 mmol)Add to 1,4-dioxane (20 mL),The reaction system was stirred at 100 C overnight.The reaction solution was then cooled to room temperature.filter,The filtrate is concentrated,The residue was purified by silica gel column chromatography (EtOAc /EtOAcCompound 1-1 (205 mg, yield: 52%) was a red liquid.

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

Reference:
Patent; Shanghai Dinuo Pharmaceutical Technology Co., Ltd.; Zhao Zhiming; Gao Daxin; Chen Shoujun; Wu Zhiheng; (105 pag.)CN108623615; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 26452-81-3, 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 26452-81-3 as follows.

A mixture of methyl 3-ethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (10520 mg, 30 mmol), 4-chloro-6-methoxypyrimidine (4645 mg, 31.5 mmol), Pd(dppf)Cl2-DCM (2449 mg, 3 mmol) and potassium phosphate tribasic monohydrate (20719 mg, 90 mmol) in water (4 mL) and DMF (150 mL) is degassed for 20 min under a nitrogen stream, then stirred at RT for 1 h 15. The RM is filtered through celite, the filtrate is concentrated under vacuum, the residue is partitioned between water and EtOAc. The organic layer is further washed with brine, dried over MgS04, filtered and concentrated. Purification by FC (heptane/EtOAc, from 1 :0 to 0:1) afforded the title compound as a yellow solid (7.87 g, 89percent). LC-MS A: tR = 0.93 min; [M+H]+ = 295.18.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26452-81-3, its application will become more common.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; BOSS, Christoph; CORMINBOEUF, Olivier; FRETZ, Heinz; LYOTHIER, Isabelle; POZZI, Davide; RICHARD-BILDSTEIN, Sylvia; SIENDT, Herve; SIFFERLEN, Thierry; (223 pag.)WO2018/210994; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 304693-64-9, 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. 304693-64-9, name is Ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate, molecular formula is C8H7F3N2O2, 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.

Intermediate B4-2-Trifluoromethyl-5-formylpyrimidine To a solution of ethyl 2-trifluoromethylpyrimidine-5-carboxylate (5.17 g) in toluene (120 ml) cooled in dry ice/acetone was added a solution of diisobutylaluminium hydride (25 wt %, 31 ml) over 15 min.The mixture was stirred at -78 C. for 45 min, then dilute HCl (2M, 120 ml) was added cautiously.After allowing the mixture to warm to room temperature diethyl ether was added.The organic phase was separated, washed with water, then brine, dried (MgSO4) and evaporated to give the title compound as a colourless solid (3.46 g, 84%).1H-NMR (CDCl3) delta 10.29 (1H, s), 9.37 (2H, s); 13C-NMR (CDCl3) delta 187.7, 159.6 (q, J=38 Hz), 159.1 (2C) 129.6, 119.2 (q, J=276 Hz).

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 304693-64-9, Ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate.

Reference:
Patent; SmithKline Beecham p.l.c.; US2004/167142; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 947533-45-1, 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 947533-45-1, name is 2-bromo-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

3-Methyl-1 ,3-butanediol (180 mg is stirred in 5 mL of Nu,Nu-dimethylformamide at 0 C, sodium hydride (6 mg of a 60% mineral oil suspension) is added and the reaction mixture is stirred for 2 h, then it is added dropwise to a solution of 2-bromo-4-fluoro- pyrimidine (300 mg) in 5 mL of N,N- dimethylformamide and the reaction mixture stirred at 0 C for 2 h again. The solvent is removed and the residue is purified by flash chromatography (hexane/ethyl acetate 90:10?70:30) to g i ve th e t it l e compound. Yield: 20 mg.

According to the analysis of related databases, 947533-45-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; WO2013/144098; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 146533-41-7, 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. 146533-41-7, name is 5-(4-Bromophenyl)-4,6-dichloropyrimidine. A new synthetic method of this compound is introduced below.

A solution of 5-(4-bromophenyl)-4,6-dichloro-pyrimidine (4.0O g, 13.2 mmol) and benzylsulfamide potassium salt (7.38 g, 32.9 mmol) in DMSO (30 mL) was stirred at rt for 24 h before being diluted with a 10% aq. citric acid solution (200 mL). The suspension that formed was filtered. The collected solid was washed well with water and dried under HV at 400C for 48 h to give the expected product as a white powder (6.15 g). 1H NMR (CDCl3): delta 4.23 (d, J = 5.9 Hz, 2H); 5.94 (t br., J = 6 Hz, IH); 7.05 (d, J = 8.2 Hz, 2H); 7.20-7.35 (m, 5H); 7.68 (d, J = 8.2 Hz, 2H); 8.61 (s, IH). LC-MS: tR = 1.02 min, [M+H]+ = 452.95.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,146533-41-7, 5-(4-Bromophenyl)-4,6-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/24906; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.130838-36-7, name is 2,6-Dichloropyrimidine-4,5-diamine, molecular formula is C4H4Cl2N4, molecular weight is 179.0074, as common compound, the synthetic route is as follows.Quality Control of 2,6-Dichloropyrimidine-4,5-diamine

A suspension of 2,6-dichloropyrimidine-4,5-diamine (16b) (4.4 g, 24.58 mmol) in water (47 ml) was heated and the solid was dissolved. The solution was cooled to 0 C and acetic acid (94 ml) was added, followed by addition of a solution of sodium nitrite (3.05 g, 44.3 mmol) in water (47 mL) during a period of 15 mm. The reaction mixture was stirred at 0 C for another 20 mm and then was extracted with EtOAc. The organics were neutralized, dried and concentrated, the crude product was purified by column chromatography (petroleum ether/ethyl acetate: from 3:1 to 2:1) to provide the title compound (16c) (3.4 g, 72.8%) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,130838-36-7, 2,6-Dichloropyrimidine-4,5-diamine, and friends who are interested can also refer to it.

Reference:
Patent; ORIC PHARMACEUTICALS, INC.; DU, Xiaohui; EKSTEROWICZ, John; FANTIN, Valeria R.; JACKSON, Erica L.; SUN, Daqing; YE, Qiuping; MOORE, Jared; ZAVOROTINSKAYA, Tatiana; (262 pag.)WO2019/90111; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 69034-08-8, name is 5-(Trifluoromethyl)pyrimidin-2-amine, molecular formula is C5H4F3N3, 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. HPLC of Formula: C5H4F3N3

To a stirred solution of the mixture A37 and A38(3, 4.5 g, l9.4mmol) in methanol(100 mL) was added drop wise H2S04(10 mL) and the reaction mixture was stirred at 80 C temperature for l6h. After completion of reaction organic solvent was evaporated and the aqueous layer was basified with Sat.NaHCCL up to pH 8 to 9 and aqueous layer was extracted with 10% MeOH in DCM and then concentrated under reduced pressure. The obtained crude was purified by column chromatography using 10% methanol in dichloromethane as eluent to afford methyl 6-(trifluoromethyl)imidazo[l,2- a]pyrimidine-2-carboxylate 1-57 and 1-58 as pink solid Yield: 0.5 g,(10%). LC-MS m/z : 245.97[M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 69034-08-8.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VADIVELU, Saravanan; RAJAGOPAL, Sridharan; BURRI, Raghunadha Reddy; GARAPATY, Shivani; SIVANANDHAN, Dhanalakshmi; THAKUR, Manish Kumar; NATARAJAN, Tamizharasan; SWAMY, Indu N; NAGARAJU, Nagendra; KANAGARAJ, Subramaniam; MOHD, Zainuddin; SARKAR, Sayantani; SAMANTA, Swapan Kumar; ., Hariprakash; (284 pag.)WO2019/102494; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia