Pyrimidines

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;,
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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. 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;,
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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;,
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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;,
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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);,
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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

Synthetic Route of 4595-61-3, Adding some certain compound to certain chemical reactions, such as: 4595-61-3, name is Pyrimidine-5-carboxylic acid,molecular formula is C5H4N2O2, 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 4595-61-3.

EXAMPLE 6. PREPARATION OF {(1S,4S)-5-[(S)-1-(2-CHLORO-4-METHOXY-3-METHYL-PHENYL)- ETHYL]-2,5-DIAZA-BICYCLO[2.2.1]HEPT-2-YL(at)-(1-OXY-PYRIDIN-4-YL)-METHANONE [0161] Isonicotinic acid N-oxide (8.3 mg, 0.06 mmol), BOP (33.2 mg, 0.075 mmol), and Et3N (17.4 pL, 0.125 mmol) are added to a solution of (lS,4S)-2-[(S)-1-(2-chloro-4-methoxy-3- methylphenyl)-ethyl]-2,5-diazabicyclo [2.2.1]heptane (14 mg, 0.05 mmol) in anhydrous DMA (1 mL). The reaction mixture is stirred at room temperature for 16 h, diluted with EtOAc, washed with aqueous NaOH IN (2 x 8 mL) and brine, dried with NazS04, filtered and concentrated under reduced pressure. The residue is purified by preparative thin layer chromatography eluting with CH2C12- MeOH-NH40H (90-9-1) to afford the title compound as a yellow oil. LC/MS: 402 (M+1).

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. 4595-61-3, Pyrimidine-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROGEN CORPORATION; WO2005/110982; (2005); A2;,
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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

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;,
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Application of 274693-26-4, 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 274693-26-4 as follows.

(1) The toluene solution of the previous product left in the 100L glass reactor was cooled to 20 C;(2) stirring was cooled to 20 C 21.409kg of hydrochloric acid and 30.75L of methanol was added to the reaction mixture of the reaction vessel; addition was completed and maintained at 20 C for 4h;(3) TLC (ethyl acetate: isooctane = 1: 1, take the upper organic point plate), FTG-3 raw material point disappears, the reaction is complete; stop stirring,Static stratification, separation of the lower methanol aqueous standby;(4) 500L reactor was added to the lower part of the lower methanol aqueous phase,With stirring, 20% aqueous potassium carbonate was added(14.202 kg of potassium carbonate and 56.81 L of purified water);Finally adjust the pH between 9;(5) adding 30.75L of ethyl acetate with stirring, stirring for 30min;Stop stirring, standing stratification, separation of the lower aqueous phase,The upper organic phase into the PE barrel backup;(6) into the lower aqueous phase reactor, 30.75L of ethyl acetate was added,Stirring 30min; stop stirring, standing stratification, separation of the lower aqueous phase;(7) The two organic phases were combined, added to a 100L glass reactor,30.75L purified water was added with stirring, stirred for 30min; stop stirring, standing stratification, separation of the lower aqueous phase;30.75L of purified water was added to the reaction kettle and stirred for 30 minutes;Stop stirring, stratification, leaving the lower aqueous phase;(8) To the organic phase, 384 g of activated carbon (5% of the amount of active carbon is used as crude product and the crude product is calculated in 100% yield) is heated to 50 C,Stir for 30min;(9) was filtered, the filtrate was evaporated under reduced pressure at 50 C solvent,Steamed until there is no liquid outflow; then add ethyl acetate 6.15L steamIn addition to the solvent, repeat 2 times, until the solid is generated, there is no liquid outflow;(10) To the residue was added 38.40L of ethyl acetate was heated to 60 C dissolved (ethyl acetate was used in an amount of 5 times the volume of the crude product, the crude product in 100% yield); The solution was transferred to a 100L glass reactor, heated To 60 C;(11) 46.08 L isooctane (isooctane in an amount of 1.2 times the volume of ethyl acetate) preheated to 60 C was added with stirring; the addition rate was controlled,Keep the internal temperature above 50 C ,During the process of solid precipitation gradually;(12) is added, cooled to 30 C with stirring, stirred for 1h;(13) and then cooled to 10 C and stirred for 2h;(14) was filtered, the reactor and the filter cake with precooled to 0 ~ 10 C of 7.68L ethyl acetate and 9.22L isooctane mixed solvent leaching;(15) The filter cake was dried under reduced pressure at 60 C for 12h to obtain crude product of ticagrelor, with white or almost white crystalline powder 6.577kg; yield 87%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,274693-26-4, its application will become more common.

Reference:
Patent; Hunan Tianji Caotang Pharmaceutical Co., Ltd.; Song Taifa; Li Linmei; Xiang Zhongyou; Weng Xiaotao; Xia Zhike; He Yanbo; Suo Chenglin; Peng Fangwei; (13 pag.)CN107337675; (2017); A;,
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