Pyrimidines

Synthetic Route of 1211443-58-1, 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.1211443-58-1, name is 2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid, molecular formula is C12H12ClN3O2, molecular weight is 265.7, as common compound, the synthetic route is as follows.

Compound VII (719.1 g, 2.70 mol, 1.0 e.q.) was added to 6 L DMF in a 10 L four-necked flask.At 0 C, DIPEA (1399.2 g, 10.83 mol, 4.0 e.q.) was added at -20 C.HATU (2566.6g, 6.75mol, 2.5e.q.) was added in batches, and the reaction was stirred for 0.5 h.At 5 C, dimethylamine methanol solution (2.5 M) 1.62 L was added dropwise, and the reaction was stirred for 1 h.LC-MS showed the reaction was completed.The reaction solution was poured into 12 L of ice water, stirred, and extracted with ethyl acetate.Wash with saturated aqueous sodium carbonate solution, wash with water, wash with dilute hydrochloric acid, and dry.The solvent was distilled off under reduced pressure, petroleum ether was filtered to obtain compound VIII as a yellow solid 617.4g,The yield was 78.1%.

Statistics shows that 1211443-58-1 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid.

Reference:
Patent; Nanjing Yaoshi Technology Co., Ltd.; Yang Guangming; Wu Shuai; Liu Cunlu; Zhu Jingwei; Yang Minmin; Wu Xihan; (17 pag.)CN110016024; (2019); A;,
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Pyrimidine – Wikipedia

Synthetic Route of 2434-53-9 , The common heterocyclic compound, 2434-53-9, name is 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione, molecular formula is C5H7N3O2, 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: Appropriate indole of 1.0 equiv, 1.1 equiv of the corresponding aminoheterocycle, and 4 equiv of TMSCl in 15 mL of anhydrous DMF was heated at 100 C under dry argon atmosphere in a pressure tube. After 6 h the solvent was removed under reduced pressure and the residue was purified by silica gel flash chromatography.

The synthetic route of 2434-53-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Knepper, Ingo; Iaroshenko, Viktor O.; Vilches-Herrera, Marcelo; Domke, Lutz; Mkrtchyan, Satenik; Zahid, Muhammad; Villinger, Alexander; Langer, Peter; Tetrahedron; vol. 67; 29; (2011); p. 5293 – 5303;,
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Related Products of 115617-41-9, 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 115617-41-9, name is 4,5-Dichloro-6-ethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

5-Chloro-6-ethyl-4-(1,4-dioxaspiro[4,5]dec-8-yloxy)pyrimidine STR27 5 g (0.16 mol) of 80% sodium hydride are added to a solution of 19 g (0.12 mol) of 4-hydroxycyclohexanone ethylene acetal in 200 ml of absolute THF and the mixture is refluxed for 1 hour. The reaction solution is then cooled to room temperature and 21.2 g (0.12 mol) of 4,5-dichloro-6-ethylpyrimidine are added dropwise. The reaction mixture is refluxed for a further 2 hours. To destroy excess sodium hydride, 20 ml of isopropanol are slowly added dropwise, and the reaction mixture, which is still warm, is stirred for a further 30 minutes. 100 ml of aqueous ammonium chloride solution are subsequently added, the aqueous phase is extracted using ether, and the combined organic phases are dried over magnesium sulfate. The solvent is concentrated in vacuo to dryness. This gives 35.0 g (93%) of a yellow oil. The crude product can be reacted further without further purification.

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 115617-41-9, 4,5-Dichloro-6-ethylpyrimidine.

Reference:
Patent; Hoechst Schering AgrEvo GmbH; US5691321; (1997); A;,
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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.5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, molecular formula is C5H3Cl2N3O, molecular weight is 192.0028, as common compound, the synthetic route is as follows.HPLC of Formula: C5H3Cl2N3O

A solution of lambda/-methylpiperazine (0.624ml), 2-amino-4,6-dichloro-5- formylpyrimidine (1.0Og) and DIPEA (0.936ml) in NMP (120ml) is stirred at room temperature for 18 hours. After addition of MTBE (400ml) the mixture is washed with a saturated solution of NaHCtheta3 (2 x 120ml) and brine (1 x 50ml), dried (MgStheta4) and concentrated to give the title compound as a colourless oil (509mg, 38%). LCMS 255/257 [M+H]+ (pH5.8), RT 1.67 mins. 1H NMR 300 MHz (d6-DMSO) (delta ppm): 10.07 (1H, s), 5.32 (2H1 bs), 3.66 – 3.58 (4H, m), 2.57 – 2.46 (4H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5604-46-6, 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; UCB PHARMA, S.A.; WO2008/74445; (2008); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 20090-69-1, 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.20090-69-1, name is 2-Chloro-4-methylpyrimidin-5-amine, molecular formula is C5H6ClN3, molecular weight is 143.57, as common compound, the synthetic route is as follows.

To a solution of 2-chloro-4-methylpyrimidin-5-amine (300 mg 2.090 mmol) in THF (20 mL) was added triphosgene (620 mg 2.090 mmol) in one portion. The mixture was stirred at 60 for 20 min. LCMS analysis showed the starting material had disappeared ES-LCMS m/z 202.1 (M+MeOH)

Statistics shows that 20090-69-1 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-4-methylpyrimidin-5-amine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; CHEUNG, Mui; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; GUAN, Huiping Amy; QIN, Donghui; WU, Chengde; GONG, Zhen; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; (391 pag.)WO2016/37578; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia