Category: pyrimidines

Application of 62802-42-0, 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. 62802-42-0, name is 2-Chloro-5-fluoropyrimidine. A new synthetic method of this compound is introduced below.

A solution of N- [(4aR,7a5)-7a-(2-fluorophenyl)-4a,5 ,6,7-tetrahydro-4H- pyrrolo[3,4-dl[1,3lthiazin-2-yllbenzamide (124.7 g, 256 mmol), DIPEA (67 mL), 5- fluoro-2-chloropyrimidine (29.3 ml, 307 mmol) in N-methylpyrrolidone (997 mL) isheated to 100 C for 16 hours. The reaction is cooled to 22 C and poured into cooled water at 10 C (10 L) keeping temperature below 15 C. A pale cream solid is collected by filtration and washed with additional water. The wet solid is dissolved in EtOAc (2 L) and transferred to a separator funnel. Sodium chloride aqueous solution 5% w/w (1 L) is added and the organic layer is separated, dried over sodium sulfate, filtered, and the filtrate evaporated under reduced pressure. The product is purified by silica gel chromatography using a gradient of 0-40% EtOAc/isohexane to give the title compound as a pale yellow solid (116 g, 70%). ES/MS (mlz): 452 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62802-42-0, 2-Chloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; COATES, David Andrew; WOLFANGEL, Craig Daniel; (55 pag.)WO2016/122968; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 13418-77-4, 2-Amino-5-methoxypyrimidine, 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, Formula: C5H7N3O, blongs to pyrimidines compound. Formula: C5H7N3O

Process 3: Under argon atmosphere, trimethylaluminum (2 mol/L hexane solution, 1.45 mL, 2.90 mmol) was added to 1,2-dichloroethane (30 mL) solution of 2-amino-5-methoxypyrimidine (220 mg, 1.74 mmol) at room temperature, and stirred at the same temperature for 80 minutes. 1,2-dichloroethane (20 mL) solution of methyl (Z)-3-acetamido-2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-2-heptenoate (227 mg, 0.58 mmol) was added dropwise thereto at room temperature followed by reflux for 17 hours under heating. An aqueous solution of ammonium chloride and chloroform were added to the reaction mixture, which was then filtered through a pad of celite. The organic layer in the filtrate was separated, and the aqueous layer was extracted with chloroform. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residues obtained were subjected to silica gel column chromatography (hexane/ethyl acetate=2:1) to obtain 2-{5-{[4-butyl-1-(5-methoxypyrimidin-2-yl)-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}benzonitrile (207 mg, 77%) as a yellow oil. 1H-NMR (CDCl3) delta: 0.95 (3H, t, J=7 Hz), 1.36-1.48 (2H, m), 1.58-1.70 (2H, m), 2.16 (3H, s), 2.63-2.72 (2H, m), 3.97 (2H, s), 4.01 (2H, s), 7.47 (1H, m), 7.60-7.71 (2H, m), 7.72-7.83 (3H, m), 8.54 (2H, s), 8.70 (1H, d, J=1 Hz).

The synthetic route of 13418-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOWA COMPANY, LTD.; US2012/165353; (2012); A1;,
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. 22536-65-8, name is 2-Chloro-5-methoxypyrimidine. A new synthetic method of this compound is introduced below., Product Details of 22536-65-8

A mixture of 2-chloro-5-methoxypyrimidine (7 g, 48.4 mmol) and ammonium hydroxide (113 mL, 2905 mmol) was heated at 100 °C in a sealed tube for 18 h. The mixture was cooled to rt and was concentrated. The residue was was purified on silica gel using 40-80 percent ethyl acetate in hexanes. The desired fractions were concentrated to give a pale yellow solid (2.75 g, 45 percent). 1H NMR (400 MHz, CDCl3) d ppm 8.02 (2 H, s), 4.80 (2 H, br. s.), 3.79 (3 H, s). LCMS (method B) tR, 0.81 min., MH+ = 293.3.

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, 22536-65-8, 2-Chloro-5-methoxypyrimidine.

Reference:
Article; Iwuagwu, Christiana; King, Dalton; McDonald, Ivar M.; Cook, James; Zusi, F. Christopher; Hill, Matthew D.; Mate, Robert A.; Fang, Haiquan; Knox, Ronald; Gallagher, Lizbeth; Post-Munson Amy Easton, Debra; Miller, Regina; Benitex, Yulia; Siuciak, Judy; Lodge, Nicholas; Zaczek, Robert; Morgan, Daniel; Bristow, Linda; Macor, John E.; Olson, Richard E.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1261 – 1266;,
Pyrimidine | C4H4N2 – PubChem,
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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 1074-41-5, name is 6-Amino-2-(methylthio)pyrimidin-4-ol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-Amino-2-(methylthio)pyrimidin-4-ol

General procedure: A mixture of 6-amino-2-(alkylthio)pyrimidin-4(3H)-one 5 (1 mmol),1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione 6 (1 mmol),arylaldehyde (1 mmol) and [gamma-Fe2O3HAp-SO3H] (0.05 g) in EtOH (10 mL) was heated under reflux. The progress of the reaction was monitored by TLC (EtOAc/petroleum: 2/1). After completion ofthe reaction, the catalyst was separated from the reaction mixture by external magnet and reused in the next run. The reaction mixture was cooled, and the solid obtained was recrystallised from EtOH/H2O to give the desired pure product. 7- (4 -Chlorophenyl ) – 4 , 5 – dioxo-2- thioxo-1,2 , 3 , 4 , 5,8 -hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile (3a): Cream powder; m.p. >300 C; IR (KBr) (numax/cm-1): 3317, 2190, 1684, 1622,1587, 1535, 1456, 1508, 1195, 812; 1H NMR (400 MHz, DMSO-d6): delta 7.69 (2H, d, J=8.8 Hz, ArH), 7.89 (2H, d, J=8.8 Hz, ArH), 13.19 (1H,s, NH), 13.59 (1H, s, NH) ppm; 13C NMR (100 MHz, DMSO-d6): delta 92.5, 98.5, 115.1, 129.1, 131.1, 135.7, 136.4, 153.8, 163.4, 165.3, 170.8,176.6 ppm. Anal. calcd for C14H7ClN4O2S (330.75): C, 50.84; H, 2.13;N, 16.94; found: C, 50.71; H, 2.03; N, 16.79%.

With the rapid development of chemical substances, we look forward to future research findings about 1074-41-5.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 32779-38-7, 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.32779-38-7, name is 2-Chloro-5-iodopyrimidine, molecular formula is C4H2ClIN2, molecular weight is 240.43, as common compound, the synthetic route is as follows.

Step-a: Synthesis of tert-butyl (2-((5-iodopyrimidin-2-yl)oxy)ethyl)carbamate Into a 500-mL round-bottom flask was placed 2-chloro-5-iodopyrimidine (10 g, 41.59 mmol, 1.00 equiv), NMP (200 mL), sodium hydroxide (3.3 g, 82.50 mmol, 2.00 equiv), and tert-butyl (2-hydroxyethyl)carbamate (6.7 g, 41.56 mmol, 1.00 equiv). The resulting solution was stirred at 100 C. until completion. The resulting solution was diluted with H2O (100 mL), extracted with of ethyl acetate (3*100 mL) and the organic layers combined, washed with brine (100 mL), dried over Na2SO4 and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:3) to deliver the title compound in 7.6 g (50%) as a brown solid.

Statistics shows that 32779-38-7 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-iodopyrimidine.

Reference:
Patent; EISAI R & D MANAGEMENT CO., LTD.; BOCK, Mark; HAO, Ming-Hong; KORPAL, Manav; NYAVANANDI, Vijay Kumar; PUYANG, Xiaoling; SAMAJDAR, Susanta; SMITH, Peter Gerard; WANG, John; ZHENG, Guo Zhu; ZHU, Ping; MITCHELL, Lorna Helen; LARSEN, Nicholas; RIOUX, Nathalie; PRAJAPATI, Sudeep; REYNOLDS, Dominic; O’SHEA, Morgan; SAMARAKOON, Thiwanka; (134 pag.)US2018/141913; (2018); 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. 126728-20-9, name is 2,4-Dichloropyrido[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 2,4-Dichloropyrido[2,3-d]pyrimidine

To a solution of 1i (106 mg, 0.50 mmol) and 2,4-dichloropyrido[2,3-d]pyrimidine (100 mg, 0.50 mmol, supplied by Combi-Blocks) in THF (2 mL) was added N,N-diisopropylethylamine (0.35 mL, 2.0 mmol). After stirring at 80 C. for 2 h, the reaction was cooled to rt, diluted with EtOAc (15 mL), washed with water (15 mL) and brine (15 mL), dried over Na2SO4, then filtered and concentrated in vacuo. The residue was subjected to silica gel chromatography eluting with hexanes-EtOAc to provide 5a. LC/MS (ESI) calculated for C16H22ClN5O: m/z 336.15, found 336.21 [M+H]+; tR=0.94 min. on LC/MS Method A. 1H NMR (400 MHz, Chloroform-d) delta 8.96 (dd, J=4.4, 1.8 Hz, 1H), 8.49 (s, 1H), 8.38 (dd, J=8.2, 1.8 Hz, 1H), 7.41 (dd, J=8.2, 4.5 Hz, 1H), 6.72 (t, J=6.9 Hz, 1H), 3.85 (dd, J=14.5, 6.7 Hz, 1H), 3.14 (dd, J=14.5, 6.3 Hz, 1H), 2.36 (td, J=13.4, 12.7, 4.4 Hz, 1H), 2.16 (s, 3H), 1.92 (td, J=13.8, 12.8, 3.9 Hz, 1H), 1.59 (s, 3H), 1.41-1.22 (m, 4H), 0.86 (t, J=7.2 Hz, 3H).

The synthetic route of 126728-20-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gilead Sciences, Inc.; Chin, Gregory; Mackman, Richard L.; Mish, Michael R.; Zablocki, Jeff; (67 pag.)US2018/65938; (2018); 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. 1445-39-2, name is 2-Amino-5-iodopyrimidine, molecular formula is C4H4IN3, 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-Amino-5-iodopyrimidine

755 mg of 1-bromo-2-butanone was dissolved in 15 ml of ethanol, 1.0 g of 2-amino-5-iodopyrimidine was added and the mixture was stirred all night by heating under reflux. After cooling down to room temperature, the solvents were distilled outunder reflux, ethyl acetate followed by saturated sodium bicarbonate aqueous solution were added. Organic layer was dried with anhydrous sodium sulfate, and the solvents were distilled outunder reduced pressure. The obtained residues were purified by silicagel column chromatography (ethyl acetate) to obtain 110 mg of the above compound as a white solid. 1HNMR(300MHz,CDCl3.)delta:1.38(3H,t,J=7.0Hz), 2.88(2H,q,J=7.0Hz), 7.25(1H,s), 8.52(1H,d,J=2.4Hz), 8.58(1H,d,J=2.4Hz) ESI-MS Found:m/z 274.0[M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 1445-39-2.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1726585; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 148550-51-0, name is Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C8H10N2O4S

General procedure: 60percent Sodium hydride (w/w) in mineral oil (0.0015 mol) was added to a mixture of appropriate III (0.001 mol) in THF (15 ml) under the condition of inert atmosphere using N2 flow at 5°C. The reaction mixture was kept for 1 h at room temperature. A solution of 2-(methylsulfonyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.0015 mol) in THF (15 ml) was slowly added to reaction mixture. The resulting reaction mixture was stirred for 2-3 h at 5°C. The distilled water (20 ml) was added. The reaction mixture was extracted (10 ml x 3) with dichloromethane. The separated organic layer was dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure to obtain crude product, recrytallized by ethyl acetate.

With the rapid development of chemical substances, we look forward to future research findings about 148550-51-0.

Reference:
Article; Rajak, Harish; Agarawal, Avantika; Parmar, Poonam; Thakur, Bhupendra Singh; Veerasamy, Ravichandran; Sharma, Prabodh Chander; Kharya, Murli Dhar; Bioorganic and Medicinal Chemistry Letters; vol. 21; 19; (2011); p. 5735 – 5738;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1445-39-2 ,Some common heterocyclic compound, 1445-39-2, molecular formula is C4H4IN3, 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.

, Step 1). 646 mg (corresponding to 3.0 mmol) of 2-bromo-4′-hydroxyacetophenone and 668 mg (corresponding to 3.0 mmol) of 2-amino-5-iodopyrimidine were dissolved in 20 mL of acetonitrile. The resulting solution was refluxed in an oil bath at 110C for 8 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 10 mL of water and 10 mL of methanol. Then, about 15 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 3 minutes using an ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure, to obtain 737 mg (corresponding to 2.19 mmol) of 2-(4′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyrimidine (

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1445-39-2, its application will become more common.

Reference:
Patent; Nihon Medi-Physics Co., Ltd.; EP2218463; (2010); 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.1312535-78-6, name is 1-(2-Chloropyrimidin-4-yl)ethanone, molecular formula is C6H5ClN2O, molecular weight is 156.5697, as common compound, the synthetic route is as follows.HPLC of Formula: C6H5ClN2O

Step 1 : l-(2-chloropyrimidin-4-yl)ethanone (1 eq) is disolved in HBr/HOAc(1 mL/ mmol) and E¾ (1.1 eq) is added drop wise. The reaction mixture is stirred for 1 hour at room temperature, ether (10 mL/mmol) was added and the mixture was cooled at 0 C. The solid is collected by filtration to afford 2-bromo-l-(2-chloropyrimidin-4-yl)ethanone.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1312535-78-6, 1-(2-Chloropyrimidin-4-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; SELEXAGEN THERAPEUTICS, INC.; VERNIER, Jean-michel; HOPKINS, Stephanie; BOUNAUD, Pierre-Yves; O’CONNOR, Patrick; MATTHEWS, David; BENDER, Steve; WO2012/125981; (2012); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia