Day: March 1, 2021

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. 1780-40-1, name is 2,4,5,6-Tetrachloropyrimidine, molecular formula is C4Cl4N2, 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. Quality Control of 2,4,5,6-Tetrachloropyrimidine

A hydroxyl group-containing tertiary amine betaine was prepared according to the method of Example 1.The tertiary amine betaine was dissolved in 500 mL of deionized water and added to a round bottom flask with mechanical stirring,Cool to about 10 C.108.5g of 2,4,5,6-tetrachloropyrimidine fine powder was added under stirring, and after stirring well,A solution of 26 g of sodium carbonate dissolved in 50 mL of deionized water was added portion wise with stirring.After adding continue to react 3 ~ 5h.Then slowly add potassium acetate to the reaction solution to precipitate the product, after filtration and washed with anhydrous ethanol,Vacuum drying to obtain a trichloropyrimidine active group tertiary amine betaine antibacterial agent.

With the rapid development of chemical substances, we look forward to future research findings about 1780-40-1.

Reference:
Patent; Hong Kong Polytechnic University; Xin Haozhong; He Liang; Gao Chang; (17 pag.)CN106928158; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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

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,
Pyrimidine – Wikipedia

Reference of 38275-55-7, Adding some certain compound to certain chemical reactions, such as: 38275-55-7, name is 5-Fluoropyrimidine-2-carbonitrile,molecular formula is C5H2FN3, 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 38275-55-7.

Intermediate 9N-( 1 -(5-Fluoropyrimidin-2-yl)vinyl)acetamide; 5-Fluoropyrimidine-2-carbonitrile (Intermediate 8, 1.0 g, 8.1 mmol) in THF (10 ml) was added a solution of MeMgBr (3.3 ml, 9.75 mmol) in ether drop wise at 0 0C. After addition, the reaction was warmed to room temperature, stirred at room temperature for 1 hour and then diluted with DCM (10 ml). Acetic anhydride (1.23 ml, 13.0 mmol) was added in one portion. The reaction was stirred at room temperature for 1 hour and 40 0C for 1 hour. Saturated sodium bicarbonate solution (10 ml) was added and extracted with EtOAc (2×20 ml). The combined organic was dried over sodium sulfate. After removal of solvent, the resulted residue was purified by column chromatography (hexane : EtOAc = 2.5 : 1) to give the title compound as a white solid (0.38 g, 26%). 1H NMR (400 MHz) 9.34 (s, IH), 8.95 (s, 2H), 6.25 (s, IH), 6.03 (s, IH), 2.11 (s, 3H). MS: Calculated: 181; Found: [M+H]+ 182.

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. 38275-55-7, 5-Fluoropyrimidine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/135786; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 49844-90-8, 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. 49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine. A new synthetic method of this compound is introduced below.

A mixture of 4-chloro-2-(methylthio)pyrimidine (102.6 g, 0.639 mol), 3-phenyl- 1 H-pyrazole-4-carbaldehyde (100.0 g, 0.581 mol), potassium carbonate (160.5 g, 1.162 mol), and dimethylformamide (700.0 mL) was stirred at 40-50C for 2 hours. Purified water (1.6 L) was slowly added to the reaction mixture, which was then stirred at room temperature for 2 hours. The resulting solid was filtered and then dried in vacuo to obtain 154.0 g of the titled compound. (Yield: 8 1.4%)1H-NMR(400MHz, CDC13) oe 10.10(s, 1H), 9.20(s,1H), 8.65(d, 1H), 7.84-7.86(m, 2H), 7.67-7.71(m, 3H), 2.65(s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,49844-90-8, 4-Chloro-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; YUHAN CORPORATION; OH, Sang-Ho; KHOO, Ja-Heouk; LIM, Jong-Chul; LEE, Seong-Ran; JU, Hyun; SHIN, Woo-Seob; PARK, Dae-Gyu; PARK, Su-Min; HWANG, Yoon-Ah; (37 pag.)WO2019/22485; (2019); A1;,
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. 696-45-7, name is 4-Amino-6-methoxypyrimidine, the common compound, a new synthetic route is introduced below. name: 4-Amino-6-methoxypyrimidine

A sealed tube was charged with 6-methoxypyrimidin-4-amine (23 mg, 0.19 mmol), methyl (1S, K or lR,45)-4-[5-(6-bromo-4-methylpyridin-2-yl)-l,3-thiazol-2-yl]-4- hydroxy-2,2-dimethylcyclohexanecarboxylate (80 mg, 0.18 mmol), XantPhos (16 mg, 0.03 mmol), cesium carbonate (119 mg, 0.36 mmol), and palladium(II) acetate (4 mg, 0.02 mmol). The vial was evacuated and backfilled with argon (3x). Fully degassed dioxane (0.7 mL) was added, the tube was sealed, and stirred at 90 ¡ãC overnight. The reaction was then cooled to room temperature, diluted with methanol, and absorbed onto 1.2 g of silica. Purification via silica gel chromatography (ethyl acetate/hexanes) afforded a 6: 1 mixture of (1R,4,S or lR,45)-l-(5-{6-[(6- methoxypyrimidin-4-yl)amino]-4-methylpyridin-2-yl} -l,3-thiazol-2-yl)-5,5-dimethyl-2- oxabicyclo[2.2.2]octan-3-one : methyl (15″,4R or lR,45)-4-hydroxy-4-(5- {6-[(6- methoxypyrimidin-4-yl)amino]-4-methylpyridin-2-yl} -l,3-thiazol-2-yl)-2,2- dimethylcyclohexanecarboxylate.; A 6: 1 mixture of (R,4S or lR,45)-l-(5- {6-[(6-methoxypyrimidin-4- yl)amino]-4-methylpyridin-2-yl} -l,3-thiazol-2-yl)-5,5-dimethyl-2-oxabicyclo[2.2.2]octan-3-one : methyl (1,S,4R or lR,45)-4-hydroxy-4-(5- {6-[(6-methoxypyrimidin-4-yl)amino]-4- methylpyridin-2-yl} -l,3-thiazol-2-yl)-2,2-dimethylcyclohexanecarboxylate (70 mg, 0.16 mmol) was taken up in methanol (2 mL) and sodium hydroxide (1M in water, 0.31 mL, 0.31 mmol) was added. The reaction was capped and stirred at 85 ¡ãC overnight. The reaction was then cooled to room temperature and acidified with 0.15 mL of 2 M aqueous hydrochloric acid. A significant amount of precipitate formed. The reaction was then diluted with water, pH3 phosphate buffer, and 5 mL of ethyl acetate and stirred for 5 minutes. The resulting slurry was filtered. The filter cake was washed with water and diethyl ether and then dried in vacuo to afford (1,S,4R or lR,45)-4-hydroxy-4-(5- {6-[(6-methoxypyrimidin-4-yl)amino]-4-methylpyridin-2-yl}-l,3- thiazol-2-yl)-2,2-dimethylcyclohexanecarboxylic acid as a white solid. MS ESI calcd. for C23H28 504S [M+H]+ 470, found 470.

The synthetic route of 696-45-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ANTHONY, Neville, J.; ANDRESEN, Brian, M.; NORTHRUP, Alan, B.; CHILDERS, Kaleen, K.; DONOFRIO, Anthony; MILLER, Thomas, A.; LIU, Yuan; MACHACEK, Michelle, R.; WOO, Hyun Chong; SPENCER, Kerrie, B.; ELLIS, John Michael; ALTMAN, Michael, D.; ROMEO, Eric, T.; GUAY, Daniel; GRIMM, Jonathan; LEBRUN, Marie-Eve; ROBICHAUD, Joel, S.; WANG, Liping; DUBOIS, Byron; DENG, Qiaolin; WO2014/176210; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1119280-68-0 , The common heterocyclic compound, 1119280-68-0, name is 2-Chlorothieno[3,2-d]pyrimidine, molecular formula is C6H3ClN2S, 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-Methoxythieno[3,2-i/]pyrimidine (17).; To a solution of 16 (146 mg, 0.86 mmol) in MeOH (20 mL) was added NaOMe (130 mg, 2.41 mmol). The solution was heated at reflux for 37 h. An additional 1.4 equiv of NaOMe (65.0 mg) was added after 24 h (Note: The reaction was complete in 7 h with comparable yields when 4.2 equiv of NaOMe were added at the start of the reaction). The reaction mixture was cooled to room temperature, quenched with 1 N aq. HC1 (2.0 mL), and extracted with DCM (4 x 10 mL). The combined organic layers were washed with H20 (10 mL), dried (MgS04), and concentrated under reduced pressure to provide 17 (125 mg, 88%) as an off-white solid: Mp 167.0-168.5 C (DCM); IR (ATR, neat) 3071, 3025, 2917, 1558, 1528, 1478, 1379, 1295, 1249, 1031, 796, 677 cm”1; 1H NMR (DMSO- 6, 300 MHz) delta 9.30 (d, 1 H, J= 0.6 Hz), 8.45 (d, 1 H, J= 5.4 Hz), 7.47 (dd, 1 H, J= 5.4, 0.7 Hz), 3.96 (s, 3 H); 13C NMR (DMSO-d6, 75 MHz) delta 163.4, 162.4, 154.8, 139.9, 124.8, 122.9, 54.6; MS (EI) m/z 166 (M+, 29), 84 (100); HRMS (EI) m/z calcd for C7H6N2OS 166.0201, found 166.0201.

The synthetic route of 1119280-68-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; WIPF, Peter; WANG, Qiming, Jan; WO2012/78859; (2012); A2;,
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

Related Products of 100644-67-5, 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. 100644-67-5, name is 4-Methoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine. A new synthetic method of this compound is introduced below.

A suspension of 6-amino-4-methoxy-1H-pyrazolo[3.4-d]pyrimidine (purine base A, 9.0g, 54.5 mmol, 1.0 eq) and a catalytic amount of ammonium sulfate in hexamethyldisilazane(HMDS, 150 mL) was refluxed for 6 h. The excess hexamethyldisilazane was removed byevaporation under reduced pressure, and the residue was dissolved in 1,2-dichloroethane (200 mL).l-O-Acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (ribose I) (35.7 g, 70.8 mmol, 1.3 eq) was added at roomtemperature. The reaction mixture was cooled to 0 C, and trimethylsilyl trifluoromethanesulfonate(TMSOTf, 29.6 mL, 163.5 mmol, 3.0 eq) was added dropwise for 30 min with stirring. The reactionmixture was stirred at room temperature overnight. Upon completion of the reaction as monitoredby TLC, the mixture was diluted with dichloromethane (200 mL) and washed with saturated sodiumbicarbonate solution. The aqueous layer was extracted with dichloromethane. The combinedorganic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.The resulting residue was purified by column chromatography to afford 10.0 g main product N9-isomer 24 as a white solid in 30.3% yield with an HPLC purity of 96%; Rf = 0.3 (petroleum ether¡Àethylacetate = 1:1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100644-67-5, 4-Methoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine, and friends who are interested can also refer to it.

Reference:
Article; Ren, Hang; An, Haoyun; Tao, Jingchao; Molecules; vol. 24; 5; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 5424-21-5, name is 2,4-Dichloro-6-methylpyrimidine. A new synthetic method of this compound is introduced below., Product Details of 5424-21-5

Cs2CO3 (6.6 g, 20.2 mmol) and 46 mL of EtOH were added to 2,4-dichloro-6-)pyrimidine (3.0 g, 18.4mmol), and the mixture was stirred for 48 hours under reflux. After filtering solids, the filtrate was purified by columnchromatography to obtain the title compound (1.88 g, 59 %).1H-NMR (CDCl3) delta 6.47 (1H, s), 4.41 (2H, q), 2.42 (3H, s), 1.39 (3H, t)

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, 5424-21-5, 2,4-Dichloro-6-methylpyrimidine.

Reference:
Patent; LG Chem, Ltd.; KIM, Young Kwan; PARK, Sang Yun; JOO, Hyun Woo; CHOI, Eun Sil; PAEK, Seung Yup; KANG, Seung Wan; KIM, Byung Gyu; LEE, Chang Seok; KIM, Sung Wook; LEE, Sang Dae; (369 pag.)EP3239143; (2017); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia