Tag: M.W:200-300

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. 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, molecular formula is C5H4Cl2N4O, 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. name: N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide

To a slurry of N-(2-amino-4,6-dichloro-5-pyrimidinyl) formamide (42g) in 2- propanol (500 ml), triethylamine (31.4g) was added at 230C. The slurry was heated to 75-8O0C. A solution of 4-amino-2-hydroxymethylbutan-l-ol (27gm, -95% purity) in a mixture of 2-propanol (120ml) and water (17.4 ml) was slowly added to the refluxing reaction mass in about 60 minutes. The mixture was stirred at 75-8O0C for 2 hrs for completion of the reaction and concentrated under reduced pressure. The resulting residue was diluted with methanol (900 ml) and treated with activated charcoal (2 g). The solution was filtered through celite and the residue was washed with methanol (80 ml). To the filtrate 10% Palladium on Carbon (50% water paste, 6g) was added. The slurry was transferred to a hydrogenation vessel and hydrogenated at ~50C and 5-6 kg/cm2 for 20 hrs. After completion of the reaction, catalyst was removed by filtration and the residue washed with methanol (50 ml). The combined filtrate was concentrated to ~130 ml under reduced pressure at < 5O0C. The concentrate was cooled to -230C and hydrogen chloride solution in methanol (54gm, 17% w/w) was added. The light yellow coloured solution was stirred for 5-10 minutes at -230C and trimethylorthoformate (96.8Og) was added. The solution was heated to about 450C and continued stirring at 45-5O0C for 4 hrs. Thereafter, a mixture of 4gm concentrated hydrochloric acid and 6 g water was added. Stirring was continued at 45-5O0C for 90 minutes, product start crystallizing after 20 minutes of stirring. The suspension was cooled to 5-80C, stirred for 60 minutes. Product was filtered and washed with prechilled methanol (30ml, O0C), and dried at 5O0C under reduced pressure to constant weight yield 27.4 g: off white powder, HPLC purity > 98.1%.

With the rapid development of chemical substances, we look forward to future research findings about 171887-03-9.

Reference:
Patent; AUROBINDO PHARMA LIMITED; WO2008/72074; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 62208-68-8, 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 62208-68-8 as follows.

Intermediate I-3 (20 g, 98.9 mmol)Dissolve in a 500 mL round bottom flask with 300 mL of phosphorus oxychloride.Cool down to -30 C,N,N-Diisopropylethylamine (25.6 g, 0.2 mol) was added slowly.The mixture was stirred under reflux for 36 hours, and then cooled to room temperature.The reaction solution was poured into ice water and extracted with ethyl acetate.The extracted organic phase is washed with a saturated sodium hydrogen carbonate solution.And remove water with sodium sulfate.The treated organic phase was concentrated to dryness to give Intermediate I-4 (10.6 g, 45%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62208-68-8, its application will become more common.

Reference:
Patent; Zhejiang Huaxian Optoelectric Technology Co., Ltd.; Zheng Xianzhe; Huang Dong; Hua Wanming; Quan Meizi; Zhao Xiaoyu; (34 pag.)CN109678868; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 14001-67-3, name is 5-Bromo-2-methylthiopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5-Bromo-2-methylthiopyrimidine

A mixture of azetidine (0.03 mL, 0.5 mmol), 5-bromo-2-(methylthio)pyrimidine (100 mg, 0.49 mmol),Xantphos (4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene) (9.9 mg, 0.02 mmol), Pd(OAc)2 (2 mg, 0.01 mmol) and NaOt-Bu (140 mg, 1 .5 mmol) in toluene (1 .7 mL) was heated at 110C. After 3h, the reaction mixture was cooled to room temperature and concentrated under vacuum. Purification (FCC, 5i02, 0-99% EtOAc in hexanes) afforded the title compound (39 mg,44%). MS(ESl): mass calcd. forC8H11N3S, 181.1; m/zfound, 182.1 [M+H]. 1H NMR (400 MHz, DMSO-d5) O 7.96 (s, 2H), 3.87 (t, J = 7.3 Hz, 4H), 2.45 (s, 3H), 2.40 -2.32 (m, 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, 14001-67-3, 5-Bromo-2-methylthiopyrimidine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHEN, Gang; CHROVIAN, Christa C.; COATE, Heather R.; DVORAK, Curt A.; GELIN, Christine F.; HISCOX, Afton; LETAVIC, Michael A.; RECH, Jason C.; SOYODE-JOHNSON, Akinola; STENNE, Brice; WALL, Jessica L.; ZHANG, Wei; (583 pag.)WO2017/139428; (2017); A1;,
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Pyrimidine – Wikipedia

Application of 183438-24-6, 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. 183438-24-6, name is 5-Bromo-2-iodopyrimidine, molecular formula is C4H2BrIN2, 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.

5-bromo-2-iodopyrimidine (16.7 g, 58.8 mmol) was dissolved in DCM (200 mL) with stirring and cooled to -78 C under N2. 2.5 M n-BuLi in hexane in hexane (23.5 mL) was added dropwise and stirred for 20 minutes at – 78 C. Intermediate 74 (10 g, 58.8 mmol) in DCM (50 mL) was cooled in a dry ice bath and added in one portion. The reaction wasstirred at -78C for 10 minutes. The reaction was quenched by addition of saturated aqueous NH4C1 solution (20 mL) and allowed to warm to r.t, saturated aqueous NH4C1 solution (50 mL) was added and the mixture was extracted with DCM (2 x 100 mL). The combined organic extracts were dried over sodium sulfate and concentrated under vacuum. The crude product was purified by column chromatography using 0 – 30 %EtOAc in heptane to afford the title compound (7.6 g, 35 %) as a yellow solid.OH (500 MHz, CDC13) 8.78 (s, 2H), 5.22 – 5.14 (m, 1H), 3.03 -2.93 (m, 2H), 2.67 – 2.58 (m, 2H), 1.22 (s, 9H).

According to the analysis of related databases, 183438-24-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; SANOFI; DE HARO GARCIA, Teresa; DELIGNY, Michael; HEER, Jag Paul; QUINCEY, Joanna Rachel; XUAN, Mengyang; ZHU, Zhaoning; BROOKINGS, Daniel Christopher; CALMIANO, Mark Daniel; EVRARD, Yves; HUTCHINGS, Martin Clive; JOHNSON, James Andrew; JADOT, Sophie; KEYAERTS, Jean; MAC COSS, Malcolm; SELBY, Matthew Duncan; SHAW, Michael Alan; SWINNEN, Dominique Louis Leon; SCHIO, Laurent; FORICHER, Yann; FILOCHE-ROMME, Bruno; (365 pag.)WO2016/50975; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 50593-91-4, 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. 50593-91-4, name is Methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below.

Preparation 31 : (¡ê)-methyl 5-(2-ethoxyvinyl)-2-(methylthio)pyrimidine-4-carboxylate A solution of (¡ê)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (Preparation 29, 4.34 g, 21 .91 mmol), methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate (Preparation 30, 3.81 g, 14.48 mmol) and Pd(dppf)CI2 DCM (505 mg, 0.618 mmol) was dissolved in THF (45 mL) and 2M sodium carbonate in water (15 mL) and heated to 65 C for 18 hours. The mixture was diluted with EtOAc and quenched with brine. The aqueous layer was extracted with EtOAc three times. The combined organic layers were washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography eluting with 0 to 10% EtOAc in cyclohexane to give the title compound (2.30 g, 63%). 1 H NMR (500 MHz, CDCI3) : delta 8.67 (s, 1 H), 6.96 (d, J = 13.1 Hz, 1 H), 6.26 (d, J = 13.1 Hz, 1 H), 4.13 – 3.81 (m, 5H), 2.60 (s, 3H), 1 .37 (t, J = 7.0 Hz, 3H). LCMS (ESI) Rt = 2.49 minutes MS m/z 255 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,50593-91-4, Methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; SOLANKI, Savade; WOODWARD, Hannah; NAUD, Sebastian; BAVETSIAS, Vassilios; SHELDRAKE, Peter; INNOCENTI, Paolo; CHEUNG, Jack; ATRASH, Butrus; WO2014/37750; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 2972-52-3, 2,4-Dichloro-5-pyrimidinecarbonyl chloride, 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, Product Details of 2972-52-3, blongs to pyrimidines compound. Product Details of 2972-52-3

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 diisopropyeihylamine (369 mg, 2,86 mmol) at 0 ¡ãC. The resulting mixture was stirred for 1 h at 0 ¡ãC. Then the solvent was removed. The residue (461rng, 94percent) was dissolved in IPA (20 ml,) and followed by the addition of trans-4-aminocyclohexanol (301.6 mg, 2.62 mmol) then DIEA (461.4 mg, 3.57 mmol) dropwiseiy. The resulting mixture was stirred at 0 ¡ãC for 90 min. After which buiyiamine (208,8 mg, 2.86 mmol) was added, followed by DIEA (461.4 mg., 3.57 mmol). The resulting mixture was stirred at room temperature for 3 h. Water was then added. The resulting mixture was extracted with EtOAc (3X). The combined organic layers were dried (Na2SO4, filtered and concentrated. The residue was purified on ISCO to give methyl 2-(butylamino)-4-((trans-4-hydroxycyclohexyl)amino)pyrimidine-5-carboxylate (682.6 mg, 89percent over 3 steps). 1H NMR (400 MHz, CDCl3) delta 9.21 (s, 1H), S.77 (s, 1H), 6.29 (s, 1H), 4.81 – 4.64 (m, 1H), 4.51 (s, 3H), 4.46-4.38 (m, 1H), 4.13-4.1 (m, 2H), 2.89-2.81 (m, 2H), 2.74 (d, J – 9.7 Hz, 2H), 2.35 – 2.25 (m, 2H), 2.23 – 2.00 (m, 6H), 1 ,67 (t, J- 7.2 Hz, 3H); 13C NMR (101 MHz, CDCl3) delta 167.9, 162,5, 161.3, 160.3, 95.5, 69.7, 51.2, 48.3, 41. L 33.8, 31 ,7, 30.3, 20.1, 13,8; MS m/z 323.20 [M+H]+

The synthetic route of 2972-52-3 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; KIREEV, Dmitri; LIU, Jing; MCIVER, Andrew Louis; WO2014/85225; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 42965-55-9, 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 42965-55-9, name is 5,6-Diaminopyrimidine-2,4(1H,3H)-dione sulfate. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 5,6-Diaminouracil sulphate (1.31 mmol, 1 eq.) was suspended in water (35 mL). The mixture wasmade alkaline using a methanolic solution of NaOH (0.65M, 3 eq.) and heated to 90 C for 15 min.A solution of diketone (1.96 mmol, 1.5 eq.) in a mixture of THF (40 mL) and water (15 mL) was addedand the mixture was stirred at 90 C for 45 min. The reaction mixture was acidified glacial acetic acid(15 mL) and heated at 90 C for another 20 h. The reaction mixture was subsequently concentrated toapproximately 1/3 of the volume, cooled in the freezer and the as-obtained suspension was filteredand the solid fraction was washed with cold water (30 mL) and cold ethanol (20 mL) to yield the crudeflavin derivative. The crude product was purified by digestion in boiling methanol. The digestedflavin derivative was further subjected to vacuum sublimation to yield the final target compound.

According to the analysis of related databases, 42965-55-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Richtar, Jan; Heinrichova, Patricie; Apaydin, Dogukan Hazar; Schmiedova, Veronika; Yumusak, Cigdem; Kovalenko, Alexander; Weiter, Martin; Sariciftci, Niyazi Serdar; Krajcovic, Jozef; Molecules; vol. 23; 9; (2018);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 353272-15-8, 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. 353272-15-8, name is 6-Chloro-5-iodopyrimidin-4-amine. A new synthetic method of this compound is introduced below.

Intermediate AA1: 3-(4-amino-6-chloropyrimidin-5-yl)prop-2-yn-1-ol A mixture of 6-chloro-5-iodopyrimidin-4-amine (prepared accordingly to the procedure reported in Tetrahedron Letters, 2010, 51, 27, 3597-3598, which is incorporated herein by reference in its entirety, 0.200 g, 0.78 mmol), 3-trimethylsiloxy-1-propyne (0.500 g, 3.94 mmol), CuI (0.052 g, 0.273 mmol) and diethylamine (0.95 mL, 8.57 mmol) in DMF (3.3 mL) was degassed and then Pd(PPh3)2Cl2 (0.097 g, 0.14 mmol) was added. The reaction was stirred at room temperature for 2 h, then diluted with EtOAc and filtered through a Celite pad. The filtrate was washed with water and brine, then dried over sodium sulfate, filtered and concentrated. The crude was purified by flash chromatography on Biotage silica-NH SNAP cartridge (cyclohexane:EtOAc=100:0 to 0:100) to afford title compound as a yellow solid (0.078 g, 0.42 mmol, 54% yield). MS/ESI+ 184.0 [MH]+, Rt=0.46 min (Method A).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,353272-15-8, 6-Chloro-5-iodopyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; BIAGETTI, Matteo; ACCETTA, Alessandro; CAPELLI, Anna Maria; GUALA, Matilde; RETINI, Michele; US2015/361100; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 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.

[00229] To a solution of 5,7-dichloro-[l,3]thiazolo[5,4-d]pyrimidine (980 mg, 4.76 mmol) in THF (20 mL) at 0 C was added benzyl alcohol (495 ul, 4.76 mmol) and sodium hydride (114 mg, 4.76 mmol, 60% in mineral oil) and stirred at r.t. for 22 h. To the reaction mixture was added water (20ml) and extracted with EtOAc (2 x 50 ml). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification by chromatography on Si02 (gradient 100:0 – 90: 10, Heptane-EtOAc) afforded the title compound (708 mg, 47%) as a white powder. [00230] Method A: LC-MS m/z = 277.85 [M + H]+; RT = 1.39 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13479-88-4, its application will become more common.

Reference:
Patent; QUARTET MEDICINE, INC.; ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL); TEBBE, Mark, Joseph; ATTON, Holly, Victoria; AVERY, Craig; BROMIDGE, Steven, Mark; KERRY, Mark; KOTEY, Adrian, Kotei; MONCK, Nathaniel, J.; MENICONI, Mirco; RIDGILL, Mark, Peter; TYE, Heather; SAIAH, Eddine; JOHNSSON, Kai, Peter; GORSKA, Katarzyna, Irena; PENG, Hairuo; MCCALL, John, Michael; (356 pag.)WO2017/59191; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
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Synthetic Route of 1211443-61-6 ,Some common heterocyclic compound, 1211443-61-6, molecular formula is C14H17ClN4O, 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: To a suspension of 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (5) (586 mg, 2 mmol) in 20 mL 1,4-dioxane were added compound 3a-f, 3i-u(2 mmol), Pd(OAc)2 (11 mg, 0.05 mmol), BINAP (62 mg, 0.1 mmol) and Cs2CO3 (978 mg, 3 mmol) and the flask was purged with Ar. Then the flask was sealed and the mixture was heated for 12 h at 100. The reaction was cooled to rt, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4a-f, 4i-o, 4r-u.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1211443-61-6, its application will become more common.

Reference:
Article; Li, Yongtao; Guo, Qingxiang; Zhang, Chao; Huang, Zhi; Wang, Tianqi; Wang, Xin; Wang, Xiang; Xu, Guangwei; Liu, Yanhua; Yang, Shengyong; Fan, Yan; Xiang, Rong; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3231 – 3237;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia