Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 115617-41-9, 4,5-Dichloro-6-ethylpyrimidine, 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, 115617-41-9, blongs to pyrimidines compound. COA of Formula: C6H6Cl2N2

(1) Synthesis of 5-chloro-6-ethyl-4-[alpha-(2,2,3-trifluorobenzo-1,4-dioxane-6-yl) ethylamino] pyrimidine 0.7 g (4.0 mmol) of 4,5-dichloro-6-ethylpyrimidine which is a material compound (IIb), 0.8 g (3.4 mmol) of 1-(2,2,3-trifluorobenzo-1,4-dioxane-6-yl)ethylamine which is a material compound (IIIc) and a catalytic amount of 4-(N,N-dimethylamino)pyridine were suspended in 5 ml of triethylamine and the suspension was heated under reflux for 5 hours. After the reaction, extraction with toluene and washing with water were conducted. After drying with anhydrous sodium sulfate, toluene was removed by evaporation under reduced pressure. The resulting oily product was purified by silicagel column chromatography (Wako gel C-200, eluted with toluene:ethyl acetate = 5:1) to give 0.5 g of the desired compound as colorless oily product (indicated in Table 12 as Compound No. 41).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115617-41-9, its application will become more common.

Reference:
Patent; UBE INDUSTRIES, LTD.; EP424125; (1991); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 22536-66-9 ,Some common heterocyclic compound, 22536-66-9, molecular formula is C5H4ClN3O, 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.

A mixture of DIEA (0.111 ml, 0.635 mmol), (S)-3-(1-aminoethyl)-6-chloroquinolin-2(1H)-one II-1 (70.7 mg, 0.317 mmol), and 2-chloropyrimidine-4-carboxamide (50 mg, 0.317 mmol) in DMSO (2 ml) was heated to 110 C. for overnight, added EtOAc, washed with water, dried and concentrated. The biotage purification with 0-5% MeOH/DCM on a 25 g column afforded (S)-2-((1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl)amino)pyrimidine-4-carboxamide I-114 (49 mg, 44.9%). 1H NMR (300 MHz, DMSO-d6): delta 11.02 (br s, 1H), 8.45 (d, J=4.7 Hz, 1H), 8.00 (br, 1H), 7.79 (br, 2H), 7.72 (s, 1H), 7.47 (d, J=8.79 Hz, 1H), 7.28 (d, J=8.8 Hz, 1H), 7.02 (d, J=4.69 Hz, 1H), 5.29 (m, 1H), 1.41 (d, J=7.04 Hz, 3H).

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. 22536-66-9, 2-Chloropyrimidine-4-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Forma Therapeutics, Inc.; Lin, Jian; Ericsson, Anna; Campbell, Ann-Marie; Gustafson, Gary; Wang, Zhongguo; Diebold, R Bruce; Ashwell, Susan; Lancia, JR., David R.; Caravella, Justin Andrew; Lu, Wei; (171 pag.)US2016/83365; (2016); A1;,
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Pyrimidine – Wikipedia

Reference of 4994-86-9, 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. 4994-86-9, name is 4-Chloro-2-methylpyrimidine, molecular formula is C5H5ClN2, 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.

A mixture of 4-chloro-2-methylpyrimidine (0.2 g, 1.556 mmol), (3-fluoro-4- methoxyphenyl)boronic acid (0.264 g, 1.556 mmol), and CS2CO3 (1.014 g, 3.11 mmol) in 1,4-dioxane (5 mL) and water (3 mL) was purged with nitrogen gas for 30 min. The reaction mixture was added PdCh (dppfJ-CfhCh adduct (0.127 g, 0.156 mmol) and was again purged with nitrogen gas for 10 min. The reaction mixture was heated at 80 C for 12 h. The reaction mixture was allowed to cool to room temperature and was concentrated under reduced pressure. The residue was taken up in ethyl acetate (50 mL) and water (40 mL), then the biphasic mixture was filtered through celite. The celite was washed with ethyl acetate (50 mL). The aqueous layer was separated out and the organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford a brown solid. The crude solid was purified by silica gel chromatography (EtOAc in pet ether) to afford 4-(3- fluoro-4-methoxyphenyl)-2-methylpyrimidine (0.128 g, 0.587 mmol, 38% yield) as a light yellow solid as an off-white color solid. LCMS (ESI) m/e 219.1 [(M+H)+, calcd for C12H12FN2O 219.1]; LC/MS retention time (method B): fe. = 0.69 min.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 4994-86-9, 4-Chloro-2-methylpyrimidine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); A1;,
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Pyrimidine – Wikipedia

Application of 10397-13-4, 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.10397-13-4, name is 4-(4,6-Dichloropyrimidin-2-yl)morpholine, molecular formula is C8H9Cl2N3O, molecular weight is 234.08, as common compound, the synthetic route is as follows.

(4S,5R)-4-Methyl-5-thiazol-2-yl-oxazolidin-2-one (4.70 g, 20.1 mmol) was dissolved in 70 mL of DMF and cooled to 0 C. NaH (964 mg, 60% in oil, 24.1 mmol) was added under argon, and the reaction mixture was stirred for 30 minutes at 0 C. 4-(4,6-dichloropyrimidin-2-yl)morpholine (3.70 g, 20.1 mmol) dissolved in 30 mL of DMF was added, and the reaction mixture was stirred for 3 hours at 0 C., followed by stirring at RT for 2 hours. The reaction was then quenched by addition of aqueous NH4Cl, followed by dilution with EtOAc; the organic solvents were separated, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (80 g SiO2) using EtOAc in hexane from 0% to 100% in order to give the title compound (3.64 g, 48%). LC-MS: [M+H] 382.2, 384.1; Rt 1.10 min; (LCMS method 1). 1H NMR (400 MHz, CHCl3-d): 7.77 (d, 1H), 7.38-7.33 (m, 2H), 5.39 (d, 1H), 5.07-4.98 (m, 1H), 3.75-3.55 (m, 8H), 1.64 (d, 3H).

Statistics shows that 10397-13-4 is playing an increasingly important role. we look forward to future research findings about 4-(4,6-Dichloropyrimidin-2-yl)morpholine.

Reference:
Patent; NOVARTIS AG; Fairhurst, Robin Alec; Furet, Pascal; Kalthoff, Frank Stephan; Lerchner, Andreas; Rueeger, Heinrich; US2014/135330; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5604-46-6, 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 5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of tert-butyl (3S)-3-ethylpiperazine-l -carboxylate (0.5 g, 2.3 mmol) and 2-amino-4,6-dichloropyrimidine-5-carbaldehyde (0.45 g) in 1,4-dioxane (8.0 mL) was added DIPEA (1.2 mL, 7.0 mmol). The reaction mixture was heated at 120C overnight in a sealed Wheaton vial, then cooled and stirred at room temperature over the weekend. The solvent was removed in vacuo, and the residue was partitioned between water and DCM. The organic layers were phase separated and concentrated in vacuo to give the title compound (0.85 g, 99%) as a yellow glass. LCMS (ES+) [M+H]+ 370, RT 1.81 minutes (method 2).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 5604-46-6, 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde.

Reference:
Patent; UCB PHARMA S.A.; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; FORD, Daniel James; FRANKLIN, Richard Jeremy; GHAWALKAR, Anant Ramrao; HORSLEY, Helen Tracey; HUANG, Qiuya; REUBERSON, James Thomas; VANDERHOYDONCK, Bart; WO2014/96423; (2014); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 1780-33-2, 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. 1780-33-2, name is 4,6-Dichloro-2,5-dimethylpyrimidine, molecular formula is C6H6Cl2N2, 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.

PREPARATION C 4-Chloro-2,5-dimethyl-6-(2,4,6-trimethylphenoxy)-pyrimidine A solution of 2,4,6-trimethylphenol (2.720 g, 20 mmol) in 60 ml of dry THF was treated with NaH (60percent in oil, 1,200 g, 30 mmol) at room temperature. After stirring at room temperature for 15 minutes, 2,5-dimethyl-4,6-dichloropyrimidine (3.34 g, 20 mmol) was added and the resulting mixture was heated at reflux for 15 hours. The mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was dried and concentrated to give 5.4528 g of beige solid. The solid was recrystallized from isopropanol to give 5.1345 g of pale yellow solid. mp 86-87° C.; high MS (C15H17ClN20) calc. 276.1025, found 276.10359. 1H NMR (CDCl3) delta 6.87 (s, 2H), 2.37 (s, 6H), 2.28 (s, 3H), 2.01 (s, 6H) ppm.

According to the analysis of related databases, 1780-33-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US6956047; (2005); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 13223-25-1, 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 13223-25-1 as follows.

Step 2: To an ice-cooled solution of 2-(4-nitro-1 H-pyrazol-1-yl)ethanol (1.90 g, 12.02 mmol) in THF (60 mL), NaH (673 mg, 16.82 mmol, 60 %) was added and the solution was stirred for 5 min at 0 C, then the ice bath was removed and the reaction mixture was stirred at rt for 30 min, before 2-chloro-4,6-dimethoxypyrimidine (2.31 g, 13.22 mmol) was added. After 40 min at rt, the reaction mixture was quenched with water and the org. solvent was removed in vacuo. The aq. layer was extracted with DCM (1 x), then acidified with 1 N HCI-solution to pH 2, and extracted with DCM (2x). The combined org. layers were washed with brine, dried (MgS04), filtered and the solvent removed under reduced pressure. Purification by crystallization (DCM-hept-mixture) yielded 4,6-dimethoxy-2-(2-(4-nitro-1 /-/-pyrazol-1- yl)ethoxy)pyrimidine as a beige solid. LC-MS conditions A: tR = 0.88 min, [M+H]+= 295.98.

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; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; BOSS, Christoph; BROTSCHI, Christine; GUDE, Markus; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi, T.; WO2012/110986; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 7226-23-5 , The common heterocyclic compound, 7226-23-5, name is 1,3-Dimethyltetrahydropyrimidin-2(1H)-one, molecular formula is C6H12N2O, 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.

A solution of diisopropylamine (29.2 mL, 0.21 mol) in dry tetrahydrofuran (186 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (62 mL) was cooled to -78 C. and then treated with a 2.5M solution of n-butyllithium in hexanes (83.4 mL, 0.21 mol). The yellow-orange reaction mixture was stirred at -78 C. for 35 min and then slowly treated with a solution of 4-(methanesulfonyl)phenyl acetic acid methyl ester (45.35 g, 0.20 mol) in dry tetrahydrofuran (186 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (62 mL). The reaction mixture turned dark in color. The reaction mixture was then stirred at -78 C. for 50 min, at which time, a solution of iodomethylcyclopentane (50.08 g, 0.24 mol) in a small amount of dry tetrahydrofuran was added slowly. The reaction mixture was then stirred at -78 C. for 50 min, and then allowed to warm to 25 C. where it was stirred for 36 h. The reaction mixture was quenched with water (100 mL), and the resulting reaction mixture was concentrated in vacuo to remove tetrahydrofuran. The remaining residue was diluted with ethyl acetate (1.5 L). The organic phase was washed with a saturated aqueous sodium chloride solution (1*500 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-methanesulfonylphenyl)propionic acid methyl ester (41.79 g, 68%) as a yellow viscous oil: EI-HRMS m/e calcd for C16H22O4S (M+) 310.1239, found 310.1230.

The synthetic route of 7226-23-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffman-La Roche Inc.; US6610846; (2003); B1;,
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. 274693-26-4, name is 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol

The intermediate TG-3 obtained in the step S3 is added to the reactor, and then dissolved in methanol, and the temperature is lowered to 2 C, and nitrogen gas is added thereto, and the methanol solution of hydrochloric acid is added dropwise under the temperature control for 2 hours. Water and ethyl acetate were added, the system was temperature-controlled at 15 C, and the liquid phase was separated. The aqueous phase was extracted twice with 5 times TG-3 weight of ethyl acetate. The organic phase was washed once with saturated aqueous sodium hydrogencarbonate and the organic layer was evaporated to dryness. After adding ethyl acetate, stirring to complete dissolution, heating to reflux, adding n-hexane dropwise, stirring and cooling to 22 C, stirring was continued for 1.5 h, filtration, and vacuum drying to obtain white solid TG-4 as a crude product; The mass ratio of TG-3, methanol, methanolic hydrochloric acid solution, water, ethyl acetate and n-hexane was 1:2.5:2.5:3:2:4.

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, 274693-26-4, 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol.

Reference:
Patent; Jiangxi Sinopharm Co., Ltd.; Yang Jianguo; Wan Yibin; Ge Youqun; Zuo Feihong; Yu Chengxiang; Yang Ming; Li Jinjin; Yu Lianxin; Liu Wei; Xie Liangliang; Liu Linhua; (19 pag.)CN108892670; (2018); A;,
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. 14080-50-3, name is Thieno[2,3-d]pyrimidin-4(3H)-one, molecular formula is C6H4N2OS, 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. Safety of Thieno[2,3-d]pyrimidin-4(3H)-one

A solution of intermediate b (5.102 g, 0.033 mol) was added to toluene (100 mL) and its phosphorus oxychloride (30 ml) 90 C for 2 hours. The reaction solution was cooled and then added dropwise to ice water, The filter cake was dried to give a yellow powder of 2.432 g in a yield of 43.4%.

With the rapid development of chemical substances, we look forward to future research findings about 14080-50-3.

Reference:
Patent; Jiangxi Science and Technology Normal University; Zhu Wufu; Zheng Pengwu; Wang Linxiao; Lan Zhou; Tang Qidong; Liu Xiaobo; Wang Caolin; Zhao Bingbing; (30 pag.)CN107253964; (2017); A;,
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