Pyrimidines

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

Related Products of 13223-25-1 ,Some common heterocyclic compound, 13223-25-1, molecular formula is C6H7ClN2O2, 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.

To a suspended tetramethyl-ammonium nitrate (11.2 g, 39.5 mmol) in methylene chloride (100 mL) was added triflic anhydride (5.4 g, 39.5 mmol), and stirred at room temperature for 2 hour. After the resultant was cooled to -78 C., a solution of 2-chloro-4,6-dimethoxypyrimidine (5.0 g, 36.0 mmol) in methylene chloride (50 mL) was added at -78 C., and continued to stirred at room temperature for 24 hours. The reaction was diluted with brine, extracted with ethyl acetate, washed with brine, dried over Na2SO4, concentrated to yield 2-chloro-4,6-dimethoxy-5-nitro-pyrimidine (25) (6.0 g, 76%). 1HNMR (DMSO-d6)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13223-25-1, its application will become more common.

Reference:
Patent; DECODE GENETICS EHF; US2009/130076; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
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

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 22536-61-4, 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 22536-61-4, name is 2-Chloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

(E)-5-Methyl-2-(prop-1-en-1-yl)pyrimidine, Example 11.01 To a 500 mL round bottomed flask was added 2-chloro-5-methylpyrimidine (12 g, 93 mmol), potassium (E)-trifluoro(prop-1-en-1-yl)borate (17.27 g, 117 mmol), and potassium phosphate (59.4 g, 280 mmol). The flask was purged with N2 (5*) and then 1,4-dioxane (200 mL) and water (20 mL) were added. The resulting yellow suspension was bubbled with Ar for 15 min and then 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium (II) chloride (Amphos, commercially available from Strem, 2.64 g, 3.73 mmol) was added, a reflux condenser was attached, and the reaction was warmed to 90 C. in an oil bath and stirred under N2 for 16.5 h. The reaction was then cooled to RT. The reaction was diluted with water (250 mL), and extracted with EtOAc (2*250 mL). The organic layers were combined, dried (MgSO4), and concentrated. The residue was purified by flash chromatography on silica gel eluting with 0-20% EtOAc/hexanes) to afford (E)-5-methyl-2-(prop-1-en-1-yl)pyrimidine 11.01 (12.96 g, 97 mmol, 100% yield) as a yellow/orange oily solid. 1H NMR (300 MHz, CDCl3) delta=8.49 (s, 2H), 7.01-7.20 (m, 1H), 6.57 (dd, J=15.6, 1.7 Hz, 1H), 2.29 (s, 3H), 1.97 (dd, J=6.8, 1.6 Hz, 3H). LCMS (ESI pos ion) m/z: 135.2 (M+H)+.

According to the analysis of related databases, 22536-61-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEDLEY, Simon J.; HOUZE, Jonathan; JUDD, Ted C.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YEH, Wen-Chen; (415 pag.)US2017/320860; (2017); 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. 31519-62-7, name is 2-Pyrimidinecarboxylic acid, the common compound, a new synthetic route is introduced below. Computed Properties of C5H4N2O2

Preparation of Intermediate 25 2211 Intermediate 25 2212 [0255] Oxalyl chloride (2.36 mL, 24.2 mmol, 1.5 eq) and a catalytic quantity of DMF were 2213 added to a solution of pyrimidine-2-carboxylic acid (2 g, 16.1 mmol) in dry DCM (30 mL) at 2214 0 C. The resulting mixture was allowed to warm to RT and stir for 3 h. The volatiles were 2215 removed in vacuo and the residue was thoroughly dried to afford pyrimidine-2-carboxylic 2216 acid chloride (2.1 g, 14.8 mmol) as a black solid. The crude material was added portion- wise 2217 to a solution of aminogaunidine sulfate (5.5 g, 22.2 mmol, 1.5 eq) in pyridine (20 mL) at 2218 0 C. The resulting mixture was allowed to warm to RT and stir for 14 h. The mixture was 2219 then neutralized with saturated aqueous NaHCOs, extracted with t-BuOH (5 x 50 mL), dried 2220 over Na2S04, filtered and concentrated in vacuo. The crude material was dissolved in water 2221 (45 mL) and the resulting solution was heated to 100 C for 24 h. The reaction mixture was 2222 then cooled to RT, extracted with t-BuOH (5 x 30 mL), dried over Na2S04, filtered and 2223 concentrated in vacuo to afford Intermediate 25 (650 mg, 25 %) as off-white solid. TLC: 30% 2224 MeOH in CHC13: Rf: 0.20.

The synthetic route of 31519-62-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERSEON, INC.; SHORT, Kevin, Michael; PHAM, Son, Minh; WILLIAMS, David, Charles; KITA, David, Ben; WO2014/145986; (2014); 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. 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