Day: March 24, 2022

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. 5267-07-2, name is 5-Pyrimidineacetic acid, molecular formula is C6H6N2O2, 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. Recommanded Product: 5-Pyrimidineacetic acid

General procedure: A flask was charged with 657 (70 mg, 0.155 mmol), 5-pyrimidineacetic acid (22 mg, 0.162 mmol) in DMF (1 ml) at 0 C was added HOBT (44 mg, 0.326 mmol) followed by EDCI (78 mg, 0.408 mmol). The resulting mixture was slowly warmed up to room temperature and stirred for overnight before it was quenched by addition of ice water (~5 mL). The white precipitate was collected by suction filtration, rinsed with more water. The crude material was purified by silica gel chromatography eluting with 0- 6% MeOH in dichloromethane to afford 675. 1H NMR (300 MHz, DMSO-d6) delta 12.75 (s, 1H), 11.32 (s, 1H), 9.11 (s, 1H), 8.76 (s, 1H), 8.22-8.19 (d, J= 9.12 Hz, 1H), 7.59-7.26 (m, 6H), 3.94 (s, 2H), 3.87 (s, 2H), 3.01 (bs, 2H), 2.90 (bs, 2H), 1.73 (bs, 4H).

With the rapid development of chemical substances, we look forward to future research findings about 5267-07-2.

Reference:
Patent; CALITHERA BIOSCIENCES INC.; LI, Jim; CHEN, Lijing; GOYAL, Bindu; LAIDIG, Guy; STANTON, Timothy, Friend; SJOGREN, Eric, Brian; WO2013/78123; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 313339-35-4, 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. 313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H4Cl2N2O2S, 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.

Reference Example 70 Production of ethyl 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carboxylate To a solution of the compound of Reference Example 69 (4.02 g, 18 mmol), amidosulfuric acid (3.50 g, 36 mmol), tert-butanol (72 mL), THF (72 mL) and water (36 mL) was added a solution of sodium chlorite (2.03 g, 18 mmol) in water (36 mL) at -10C, and the mixture was stirred for 10 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with 1% aqueous sodium thiosulfate solution and brine, dried over magnesium sulfate, and concentrated under reduced pressure to give 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carboxylic acid as a crude product. To a solution of this crude product in THF (50 mL) were added oxalyl chloride (2.36 mL, 27 mmol) and DMF (1 drop), and the mixture was stirred at room temperature for 1 hr. Water was added thereto, and the mixture was extracted twice with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. To the residue were added ethanol (50 mL) and triethylamine (3.76 mL, 27 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, aqueous sodium hydrogen carbonate solution was added thereto, and the mixture was extracted twice with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=99:1?90:10) to give the title compound (3.28 g, 68%) as a pale-yellow oil. 1H NMR (300 MHz, CDCl3) delta:1.41 (3 H, t, J = 7.2 Hz), 2.59 (3 H, s), 4.45 (2 H, q, J = 7.1 Hz).

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 313339-35-4, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2471793; (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. 87789-35-3, name is 5,7-Dichloro-2-(methylthio)thiazolo[4,5-d]pyrimidine. A new synthetic method of this compound is introduced below., COA of Formula: C6H3Cl2N3S2

The crude brown solid was slurried in methanol and morpholine (6eq) was added. The solution was stirred at room temperature for 30 min, solvent was removed under vacuum and ethyl acetate was added. The organic was washed with saturated sodium bicarbonate solution. Both the precipitate and the organic layers contained product and were subjected to silica gel chromatography to yield 5-chloro-2-(methylthio)-7-morpholinothiazolo[4,5-d]pyrimidine 78 and 5-chloro-2,7-dimorpholinothiazolo[4,5-d]pyrimidine 79.

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, 87789-35-3, 5,7-Dichloro-2-(methylthio)thiazolo[4,5-d]pyrimidine.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN – LA ROCHE AG; WO2009/42607; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 16019-34-4, Adding some certain compound to certain chemical reactions, such as: 16019-34-4, name is 7-Benzyl-4-chloro-7H-pyrrolo[2,3-d] pyrimidine,molecular formula is C13H10ClN3, 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 16019-34-4.

General procedure: A typical procedure for the preparation of 3a:2-bromopropane (74 mg, 0.6 mmol) was added to a solution of 1a (92 mg, 0.6 mmol) and K2CO3 (110 mg, 0.8 mmol) in 5 mL DMF at 70 C. According to TLC the reaction went to completion after 4 h. The mixture was extracted with ethyl acetate (3 * 10 mL). The combined organic layers were washed with brine(10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give the crude product 2a, which was added to a solution of amino-phenol(66 mg, 0.6 mmol) and Cs2CO3 (585 mg, 1.8 mmol) in 10 mL DMSO without further purification. After stirring for 6 h at 80 C, the mixture was cooled to room temperature and extracted with ethyl acetate (3 * 10 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give the crude product, which was further purified by column chromatography(petroleum ether/ethyl acetate 2:1) to afford compound 3a as a brown solid(121 mg, 75% over two steps): 1H NMR (300 MHz, CDCl3) delta 8.44 (s, 1H), 7.16 (d, J = 3.6 Hz, 1H), 7.02 (d, J = 8.9 Hz, 2H), 6.73 (d, J = 8.9 Hz, 2H), 6.39 (d, J = 3.6 Hz, 1H), 5.11 (m, 1H), 3.70 (s, 2H), 1.51 (d, J = 6.8 Hz, 6H).; 13C NMR (100 MHz, d6-DMSO) delta 162.5, 151.5, 150.0, 146.3, 142.7, 124.5, 122.2, 114.3, 104.6, 98.0, 46.0, 22.3.; HRMS [M]+ calcd for C15H16N4O268.1324, found 268.1326. The purity of the compound was >98% by HPLC.

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. 16019-34-4, 7-Benzyl-4-chloro-7H-pyrrolo[2,3-d] pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Yang; Fang, Jianping; Cai, Haiyan; Xiao, Fei; Ding, Kan; Hu, Youhong; Bioorganic and Medicinal Chemistry; vol. 20; 18; (2012); p. 5473 – 5482;,
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 114040-29-8, name is Ethyl 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Ethyl 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate

In 100ml RB flask 2-amino triazole 5-ethyl carboxylate (5gm) was taken. To it 2,4-pentandione (4.1ml) was added followed by addition of piperidine (4ml). This reaction mixture was refluxed for 3 daysunder nitrogen. Reaction mixture was cooled. Solvent from the RM was evaporated. To the residue water was added and neutralized with 6N HCl, solid precipitated. It was filtered and washed with diethyl ether and dried to give pure product as white solid (4 g, 55 %).

With the rapid development of chemical substances, we look forward to future research findings about 114040-29-8.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 29939-37-5, 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. 29939-37-5, name is 4-Hydroxy-6-hydrazinylpyrimidine. A new synthetic method of this compound is introduced below.

A mixture comprising 5.0 g (39.6 mmol) 6-hydrazinopyrimidin-4-ol/6- hydrazinopyrimidin-4(1 H)-one (CAS-No: 29939-37-5), 5.12 g pentan-3-one and 80.8 mL ethanol was heated under reflux for 2 hours. After cooling to 3C, the precipitated solid was filtered off and washed with diethyl ether to give 5.82 g (72%) of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29939-37-5, 4-Hydroxy-6-hydrazinylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KLAR, Ulrich; WORTMANN, Lars; KETTSCHAU, Georg; PUeHLER, Florian; LIENAU, Philip; PETERSEN, Kirstin; HAeGEBARTH, Andrea; SUeLZLE, Detlev; GRAHAM, Keith; RICHTER, Anja; WO2014/48869; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 882670-89-5, 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 882670-89-5, name is 6-Bromopyrido[2,3-d]pyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 6-(3 ,5 -dimethoxyphenyl)pyrido [2,3-d]pyrimidin-2-amine. A mixture of 6-bromopyrido[2,3-d]pyrimidin-2-amine (1.0 g, 4.46 mmol), 3,5- dimethoxyphenylboronic acid (1.2 g, 6.70 mmol), PdC12(dppf) (364 mg, 0.446 mmol) and potassium carbonate (1.8 g, 13.39 mmol) in 1,4-dioxane/water (4 mL/1 mL) was degassed withnitrogen for 5 mm and stirred at 110 C for 30 mm under microwave. The reaction mixture was cooled to RT, and concentrated to afford a crude product, which was purified by silica gel column chromatography (ethyl acetate:petroleum ether = 4: 1) to afford 6-(3,5- dimethoxyphenyl)pyrido[2,3-d]pyrimidin-2-amine as a yellow solid (400 mg, 31%). MS (ES+) C15H14N402 requires: 282, found: 283 [M+H].

According to the analysis of related databases, 882670-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUEPRINT MEDICINES; BIFULCO, Neil, Jr.; BROOIJMANS, Natasja; HODOUS, Brian, L.; KIM, Joseph, L.; MIDUTURU, Chandrasekhar, V.; WO2014/11900; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3438-61-7 ,Some common heterocyclic compound, 3438-61-7, molecular formula is C5H7N3, 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.

To a solution of 4-methylpyrimidin-5-amine (1) (3.0 g, 27.5 mmol) and pyridine (10.9 g, 0.137 mol) in DCM (30 mL) was added methanesulfonyl chloride (6.3 g, 55.0 mmol) at 0 C. and the resulting mixture was stirred at 20 C. for 3 hours. TLC showed the reaction was completed. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give N-(4-methylpyrimidin-5-yl)methanesulfonamide (2) (1.0 g, 19.4%) as yellow solid. 1H NMR (400 MHz, CHCl3-d) delta ppm 8.98 (s, 1H), 8.76 (s, 1H), 6.68 (br s, 1H), 3.13 (s, 3H), 2.61 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3438-61-7, its application will become more common.

Reference:
Patent; ESSA Pharma, Inc.; Zhou, Han-Jie; Virsik, Peter; (216 pag.)US2020/123117; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 313339-35-4, 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 313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 3pyrimidin-5-yl1carbonyl}amino]phenyl>cvclohexyl acetate.A 50-mL 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was charged with a solution of 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid (700 mg, 2.93 mmol, 1.50 equiv) and N^V-dimethylformamide (1 drop) in dichloromethane (10 mL). The solution was treated with oxalyl chloride (750 mg, 5.91 mmol, 3.00 equiv) dropwise with stirring, stirred for 2 h at room temperature and then treated with a solution of Intermediate 2 (800 mg, 1.97 mmol, 1.00 equiv) in dichloromethane (10 mL) and DIEA (2 mL) dropwise with stirring at 0C. The resulting solution was stirred for an additional 1 h at room temperature, concentrated under vacuum and the residue was purified by chromatography on silica gel (1 :10 ethyl acetate/petroleum ether) to afford the title compound as a colorless oil. HPLC/MS: 626.31 (M+H); Rt 4.78 min (LC4).

According to the analysis of related databases, 313339-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GRAHAM, Thomas, H.; SHEN, Dong-Ming; NARGUND, Ravi, P.; DEVITA, Robert, J.; YU, Yang; LIU, Wensheng; WO2012/122075; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 199678-12-1, Adding some certain compound to certain chemical reactions, such as: 199678-12-1, name is 4-Pyrimidin-2-yl-benzoic acid,molecular formula is C11H8N2O2, 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 199678-12-1.

General procedure: This compound was prepared by means of a procedure similar to that used for 7g and 7a. Under an argon atmosphere, diethyl cyanophosphonate (DEPC) (0.09 mL, 0.61 mmol) and triethylamine (0.18 mL, 1.30 mmol) were added to a solution of compound 9 (246 mg, 0.47 mmol) and 4-(2-pyridyl)benzoic acid (94 mg, 0.47 mmol) in dehydrated N,N-dimethylformamide (10 mL) at 0 C. The reaction mixture was left to stand overnight, then poured into a saturated aqueous solution of sodium hydrocarbonate, and the whole was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluant; n-hexane/ethyl acetate = 1:2 v/v) to afford the intermediate compound.

According to the analysis of related databases, 199678-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ohashi, Masao; Oyama, Takuji; Putranto, Endy Widya; Waku, Tsuyoshi; Nobusada, Hiromi; Kataoka, Ken; Matsuno, Kenji; Yashiro, Masakazu; Morikawa, Kosuke; Huh, Nam-Ho; Miyachi, Hiroyuki; Bioorganic and Medicinal Chemistry; vol. 21; 8; (2013); p. 2319 – 2332;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia