Month: January 2021

Electric Literature of 5909-24-0, 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. 5909-24-0, name is Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

260 mL of N,N-diisopropylethylamine and 106 g of the hydrazine obtained in the above 1 were added to tetrahydrofuran (1.5 L) solution of 142 g of ethyl 4-chloro-2-(methylthio)pyridine-5-carboxylate, and stirred with heating under reflux for 18 hours. After cooled to room temperature, the reaction solution was evaporated under reduced pressure, and 500 mL of diethyl ether was added to the residue, and the precipitated solid was separated through filtration. The filtrate was evaporated under reduced pressure, the residue was cooled in an ice bath, 400 mL of trifluoroacetic acid was gradually added thereto, and stirred at room temperature for 1 hour and then at 70 C. for 1 hour. The reaction solution was evaporated under reduced pressure, 500 mL of ethanol was added thereto and cooled in an ice bath, and 1.0 L of 6 N sodium hydroxide solution was added thereto and stirred at room temperature for 15 minutes. Cooled in an ice bath, the reaction solution was made acidic with 400 mL of concentrated hydrochloric acid, and then evaporated under reduced pressure. The residue was partitioned in chloroform and water, and the chloroform layer was extracted, washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the formed yellow solid was taken out through filtration, washed with ethanol and diethyl ether, and dried to obtain 99.1 g of the entitled compound as a yellow solid.1H-NMR (400 MHz, DMSO-d6) ?: 8.66 (1.0H, brs), 5.83 (1.0H, ddt, J=17.1, 9.8, 5.4 Hz), 5.13 (1.0H, d, J=9.8 Hz), 5.06 (1.0H, d, J=17.1 Hz), 4.34 (2.0H, d, J=5.4 Hz), 2.51 (3.0H, s).ESI-MS Found: m/z[M+H]+ 223.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5909-24-0, Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Sagara, Takeshi; Otsuki, Sachie; Sunami, Satoshi; Sakamoto, Toshihiro; Niiyama, Kenji; Yamamoto, Fuyuki; Yoshizumi, Takashi; Furuyama, Hidetomo; Goto, Yasuhiro; Bamba, Makoto; Takahashi, Keiji; Hirai, Hiroshi; Nishibata, Toshihide; US2007/254892; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4983-28-2, 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. 4983-28-2, name is 2-Chloro-5-hydroxypyrimidine, molecular formula is C4H3ClN2O, 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.

To a solution of 4-methanesulfonyloxymethylpiperidine-l-carboxylic acid tert-butyl ester (Preparation 23, 1.47g, 5.0mmol) and 2-chloropyrimidin-5-ol (0.65g, 5.0mmol) in DMF (80mL) was added potassium carbonate (0.83g, 6.0mmol) and the reaction was heated to 80C until complete. The solvent was removed in vacuo, and the resulting residue was re- dissolved in EtOAc (300mL). The solution was washed with 1M NaOH solution (200mL), brine (200mL), then dried (MgS04) and the solvent was removed in vacuo. Purification by column chromatography (IH:EtOAc, 70:30) afforded the title compound: lH NMR delta?(400MHz, CDCI3): 8.30 (s, 1H), 4.18 (br. s., 2H), 3.92 (dd, J=6.25, 3.51 Hz, 2H), 2.78 (t, J=12.30 Hz, 2H), 2.09 – 1.95 (m, 1H), 1.84 (d, J=12.89 Hz, 2H), 1.49 (s, 9H), 1.41 – 1.24 (m,2H).

According to the analysis of related databases, 4983-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROSIDION LIMITED; BARBA, Oscar; BELL, James, Charles; DUPREE, Tom, Banksia; FRY, Peter, Timothy; BERTRAM, Lisa, Sarah; FYFE, Matthew, Colin, Thor; GATTRELL, William; JEEVARATNAM, Revathy, Perpetua; KEILY, John; KRULLE, Thomas, Martin; MCDONALD, Russell, Walker; MORGAN, Trevor; RASAMISON, Chrystelle, Marie; SCHOFIELD, Karen, Lesley; STEWART, Alan, John, William; SWAIN, Simon, Andrew; WITHALL, David, Matthew; WO2011/147951; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4994-86-9, 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 4994-86-9 as follows.

General procedure: To a well stirred 8-aminoquinoline (1 mmol) indry DMF (5 mL), sodium hydride (1.2 mmol, 60% in mineral oil) was added at 0 C.After 10 min stirring, the corresponding heterocyclic chloro compound (1.2mmol) was added and stirred for 10 min at rt then heated at 60 C for 5-12 h.Upon completion, the reaction mixture was poured into crushed ice and theresulting solid was filtered, washed with water and dried under vacuum. Thesolid was triturated with methanol and dried under vacuum to afford targetcompound as a solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4994-86-9, its application will become more common.

Reference:
Article; Kannan, Murugan; Raichurkar, Anandkumar V.; Khan, Fazlur Rahman Nawaz; Iyer, Pravin S.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 5; (2015); p. 1100 – 1103;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 180869-38-9, 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 180869-38-9, name is 4-(Dimethoxymethyl)-N-methylpyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

To the 2M solution of methylamine in THF (3 mL) 232 mg 4-(dimethoxymethyl)-2- methylsulfonyl-pyriinidine (Preparation 9a3, 1.00 mmol) was added and it was stirred at room temperature for lh. The reaction mixture was concentrated under reduced pressure, the residue was diluted with EtOAc and washed with brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. To the residue 3 mE 2N HC1 was added and it was stilTed at 60C for 2h. Than it was cooled to 0C, the pH was adjusted to 9 using 2N NaOH solution, and then 76 mg sodium borohydride (2.0 mmol) was added and the mixture was stirred for lh. The reaction mixture was extracted with EtOAc, thecombined organic layers were dried over MgSO4 and concentrated under reduced pressure to give the title product.MS: (M+2H) 141.4.

According to the analysis of related databases, 180869-38-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; KOTSCHY, Andras; SZLAVIK, Zoltan; CSEKEI, Marton; PACZAL, Attila; SZABO, Zoltan; SIPOS, Szabolcs; RADICS, Gabor; PROSZENYAK, Agnes; BALINT, Balazs; BRUNO, Alain; GENESTE, Olivier; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; PERRON-SIERRA, Francoise; WO2015/97123; (2015); 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. 1197193-30-8, name is Ethyl 5-bromopyrimidine-2-carboxylate, molecular formula is C7H7BrN2O2, 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. Computed Properties of C7H7BrN2O2

To a suspension of the ethyl 5-bromopyrimidine-2-carboxylate (700 mg, 3 mmol), 4,4,5,5-tetramethyl-2-(prop-l-en-2-yl)-1,3,2-dioxaborolane (1.5 g, 9 mmol), andK2C 0 3 (2.1 g, 15 mmol) in DMF (5 mL) and water (1 mL), was added Pd(dppfC12) (250 mg, 0.3 mmol). The resulting mixture was degassed (N2) for 2 min and then heated to heated to 120 C. for 1 h. After cooling to room temperature,the reaction mixture was diluted with MeOH and filteredthrough celite. The filtrate was used directly for next step. MS: (ES) m/z 165.2 (M+H+).

With the rapid development of chemical substances, we look forward to future research findings about 1197193-30-8.

Reference:
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1683-85-8, 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 1683-85-8, name is 5-Fluoropyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 5-fluoropyrimidin-2-amine (8.2 g, 72.1 mmol) and sodium hydride (5.8 g, 144 mmol) in THF (100 mL) was added 2,4-dichloro-6-methyl-3-nitropyridine (15 g, 72.1 mmol). After stirring for 10 h, ethanol was added. Silica gel chromatography (5:1Hexane:EtOAc) provided the product as a yellow solid (12.8 g, 63%).

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 1683-85-8, 5-Fluoropyrimidin-2-amine.

Reference:
Patent; Janssen Pharmaceutica NV; Alcazar Vaca, Manuel Jesus; Andres Gil, Jose Ignacio; Chrovian, Christa C.; Coate, Heather R.; De Angelis, Meri; Dvorak, Curt A.; Gelin, Christine F.; Letavic, Michael A.; Savall, Brad M.; Soyode-Johnson, Akinola; Stenne, Brice M.; Swanson, Devin M.; US2014/275015; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1193-21-1, 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 1193-21-1, name is 4,6-Dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

4,6-Dichloropyrimidine (20.85 g, 139 mmol) and 7 N Ammonia in methanol (200 mL) were heated to 85 C in a sealed glass bomb for 16 h. The reaction was cooled to ambient temperature, the solvent evaporated, and the residue recrystalized from water yielding compound 17 (12.07 g, 93.17 mmol, 67% yield). 1H NMR (400 MHz, DMSO-D6): S 6.43 (s, 1 H), 7.22 (s, 2 H), 8.18 (s, 1 H). ESI-MS mXz : 130 (M + H) +.

According to the analysis of related databases, 1193-21-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNESIS PHARMACEUTICALS, INC.; MORROW, Joelle; WO2005/34840; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 157335-93-8, 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. 157335-93-8, name is 4,6-Dimethylpyrimidine-5-carboxylic acid, molecular formula is C7H8N2O2, 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.

To a solution of 110a (51 mg, 0.10 mmol) and DCM (5 mL) was added TFA (1 mL) and the reaction was stirred at RT for 6 h. The solvent was evaporated in vacuo and the residue partitioned between 5M KOH and EtOAc. The phases were separated and the aqueous extracted two times with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated to afford 110b. To a solution of 110b (17 mg, 0.04 mmol), 4,6-dimethylpiperidine-5 carboxylic acid (7 mg, 0.044 mmol), HOBt (7 mg, 0.052 mmol) and DMF (0.5 mL) was added EDCI (10 mg, 0.052 mmol) followed by DIPEA (21 mul, 0.12 mmol). The reaction was stirred at RT for 18 h. The reaction was quenched with water and diluted with EtOAc. The phases were separated and the aqueous extracted two times with EtOAc. The combined EtOAc extracts were dried (Na2SO4), filtered and evaporated. The crude material was purified by Prep HPLC to give 8.1 mg (37%) of IV-13 as a white solid: MS (ESI), m/z 542 (M+H).

According to the analysis of related databases, 157335-93-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rotstein, David Mark; Melville, Chris Richard; US2008/249087; (2008); 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. 1100318-96-4, name is 4-Iodo-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Product Details of 1100318-96-4

Description 84; 1,1 -Dimethylethyl (4-iodo-7H-pyrrolo[2,3-cf]pyrimidin-7-yl)acetate (D84)To a solution of 4-iodo-7H-pyrrolo[2,3-d]pyrimidine (3 g, 8.07 mmol) in dry N, N- dimethylformamide (50 ml.) was added sodium hydride (0.71 g, 17.75 mmol) portionwise and the mixture stirred for 10 minutes to give a clear solution. tert-Butyl bromoacetate (2.62 ml_, 17.75 mmol) was added and the mixture stirred for 1 hour. Ethyl acetate (250 ml.) was added and washed with water (2×200 ml_). Dried over magnesium sulfate and solvent evaporated to give a yellow oil. A small amount of solid started to form. Ether (10 ml.) was added followed by hexane (40 ml.) and a white solid slowly precipitated. After collection and washing with hexane the title compound was obtained as a white solid. LC/MS (ES+ve): [M+H]+ at m/z 360 (Ci2H14IN3O2 requires [M+H]+ at m/z 360).

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, 1100318-96-4, 4-Iodo-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/80682; (2009); 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. 5750-76-5, name is 2,4,5-Trichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C4HCl3N2

General procedure: To a solution of 2,4-dichloro-5-fluoropyrimidine (0.5 g, 2.99 mmol) and (2-aminophenyl)dimethylphosphineoxide (0.323 g, 1.907 mmol) in DMF (6.36 mL) wasadded potassium carbonate (0.828 g, 5.99 mmol). The reactionmixture was stirred at 70 C for overnight. After completion of thereaction, the resulting mixture was cooled to room temperature,quenched with water, extracted with DCM and washed with brine.The combined organic layer was dried over Na2SO4, filtered andconcentrated under reduced pressure. The residue was purified byflash column chromatography on silica gel (0-20% MeOH in DCM)to give 3f as a yellowish solid (0.178 g, 31%).

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, 5750-76-5, 2,4,5-Trichloropyrimidine.

Reference:
Article; Jang, Jaebong; Son, Jung Beom; To, Ciric; Bahcall, Magda; Kim, So Young; Kang, Seock Yong; Mushajiang, Mierzhati; Lee, Younho; Jaenne, Pasi A.; Choi, Hwan Geun; Gray, Nathanael S.; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 497 – 510;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia