Category: pyrimidines

Synthetic Route of 1209459-80-2, 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. 1209459-80-2, name is Methyl 6-bromopyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below.

Tripotassium phosphate (2eq) was added in one portion to a stirred solution of 8-chloro-6-(4,4,5,5-tetramethyl- [l,3,2]dioxaborolan-2-yl)-chroman (leq) and methyl 4-bromopyridine-2-carboxylate (2eq) in DMF (lOvol). The mixture was degassed with nitrogen for 5 minutes, after which time Pd(dppf)2C12 (0.2eq) was added in one portion, the mixture was then heated to 60oC and stirred at this temperature for 16 hours under a nitrogen atmosphere. After this time the reaction mixture was cooled to room temperature and partitioned between ethyl acetate (5 vol) and water (5 vol). The organic layer was separated, washed sequentially with water (5vol) then brine (5vol) before being dried (MgS04), filtered andconcentrated. The resulting residue was purified using a Biotage Isolera (lOOg silica column eluting with a gradient from 0% heptane to 80% DCM / 20% heptane) to give the desired compound as a white solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1209459-80-2, Methyl 6-bromopyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; COURTNEY, Stephen Martin; PRIME, Michael; MITCHELL, William; BROWN, Christopher John; DE AGUIAR PENA, Paula C.; JOHNSON, Peter; DOMINGUEZ, Celia; TOLEDO-SHERMAN, Leticia M.; MUNOZ, Ignacio; WO2013/33085; (2013); A1;,
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Related Products of 1159818-57-1, 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 1159818-57-1, name is 4-Amino-6-bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 6-bromopyrimidin-4-amine (1.01 g, 5.80 mmol) and ammonia solution (25 mL) was stirred in a sealed tube at 125 C overnight, then cooled down to rt and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v) = 1/15) to give the title compound as a yellow solid (0.46 g, yield 72%).MS (ESI, pos. ion) m/z: 111.2 [M+H]+; (ppm): 7.82 (s, 1H), 6.10 (s, 4H), 5.39 (s, 1H).

According to the analysis of related databases, 1159818-57-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
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Application of 3438-55-9, 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. 3438-55-9, name is 5-Bromo-4-chloro-6-methylpyrimidine. A new synthetic method of this compound is introduced below.

PREPARATIVE EXAMPLE 6 dl-5-bromo-6-methyl-4-(alpha-methylbenzylamino)pyrimidine (compound number 314) 2.0 g (0.02 mol) of triethylamine and 2.4 g (0.02 mol) of dl-alpha-methylbenzylamine were added to a solution of 4.15 g (0.02 mol) of 5-bromo-4-chloro-6-methyl-pyrimidine in 50 ml of benzene, and the mixture was refluxed with stirring for 5 hours. Upon completion of the reaction, the reaction product was washed with water, dried over anhydrous sodium sulphate and the benzene was distilled off to leave an oil. This oil was then caused to crystallize using column chromatography (Wakogel C-200, eluted with a 1:1 mixture of benzene and ethyl acetate). Crystals were obtained and recrystallized from n-hexane to give 2.6 g of the desired product in the form of pale yellow prisms melting at 85-87 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3438-55-9, its application will become more common.

Reference:
Patent; Sankyo Company, Limited; Ube Industries, Limited; US4435402; (1984); A;,
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Synthetic Route of 1074-68-6 ,Some common heterocyclic compound, 1074-68-6, molecular formula is C6H6N2OS, 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.

Preparation of 3-hydroxy-3-(2-methylsulfanyl-pyrimidin-4-yl)-propionic acid tert-butyl ester (18): To a cold (0 C.) solution of diisopropylamine (5.7 mL, 40.5 mmol) in THF (130 mL) is added dropwise n-butyllithium (16.2 mL of a 2.5 M solution in hexanes, 40.5 mmol). The mixture is stirred for 45 min at 0 C., then the solution is cooled to -78 C. tert-Butyl acetate (5.5 mL, 40.5 mmol) is added dropwise to the reaction mixture. After stirring 40 min at -78 C., a solution of 2-methylsulfanyl-pyrimidine-4-carbaldehyde (5.0 g, 32.4 mmol) is added dropwise. After 30 min at -78 C., the solution is poured into aqueous saturated NH4Cl. The aqueous phase is extracted with EtOAc. The organic phase is dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified over silica (5% EtOAc/hexanes, followed by 20% EtOAc/hexanes) to afford 7.2 g (82% yield) of the desired product. 1H NMR (300 MHz, CDCl3) delta 8.52 (d, J=5.1 Hz, 1H), 7.22 (d, J=5.1 Hz, 1H), 5.00 (dd, J=8.4, 3.6 Hz, 1H), 2.93 (dd, J=16.5, 3.6 Hz, 1H), 2.70 (dd, J=16.5, 7.8 Hz, 1H), 2.58 (s, 3H), 1.46 (s, 9H); ESI+ MS: m/z (rel intensity) 271.1 (85, M++H).

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. 1074-68-6, 2-Methylsulfanylpyrimidine-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Procter & Gamble Company; US2005/113392; (2005); 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. 830346-47-9, name is 1-(2-Fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione, molecular formula is C13H10F4N2O2, 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 1-(2-Fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione

Step 1D: Preparation of 5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6- methylpyrimidine-2,4 (1H,3H)-dione 1-1; Bromine (16.5 mL, 0.32 mmol) was added to 1-[2-fluoro-6- (trifluoromethyl)benzyl]-6-methylpyrimidine-2,4(IH,3H)-dione 1c (48.5 g, 0.16 mol) in 145 mL of acetic acid. The resulting mixture became clear then formed precipitate within an hour. After 2 hours stirring, the yellow solid was filtered and washed with cold EtOAc to an almost white solid. The filtrate was washed with sat. NaHC03 and dried over Na2S04. Evaporation gave a yellow solid which was washed with EtOAC to give a light yellow solid. The two solids were combined to give 59.4 g of 1-1 (0.156 mol) total. 1H NMR (CDC13) No. 2.4 (3H, s), 5.48 (2H, s), 7.25 – 7.58 (3H, m), 8.61 (1H, s) ; MS (CI) m/z 380.9 (MH+).

With the rapid development of chemical substances, we look forward to future research findings about 830346-47-9.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2005/113516; (2005); A1;,
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Application of 87789-35-3, 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 87789-35-3, name is 5,7-Dichloro-2-(methylthio)thiazolo[4,5-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of ethyl 5-chloro-2-(methylthio)thiazolo[4,5-d]pyrimidine-7-carboxylate: The title compound was prepared from 5,7-dichloro-2-(methylthio)thiazolo[4,5-d]pyrimidine (commercially obtained from Combi-Block, San Diego, CA) using chemistry similar to that described in Example 1. ESI MS: m/z [M+H+] for C9H8ClN3O2S2, calcd 290.0, found 290.1.

According to the analysis of related databases, 87789-35-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Corvus Pharmaceuticals, Inc.; LI, Zhihong; FILONOVA, Lubov, Konstantinovna; VERNER, Erik; (375 pag.)EP3616753; (2020); A1;,
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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. 34415-10-6, name is 2-Methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 2-Methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid

A mixture of 6-hydroxy-2-methylpyrimidine-4-carboxylic acid (500 mg) and phosphorus oxychloride (5 mL) was heated under reflux under a nitrogen atmosphere for 2 hr. The solvent was evaporated under reduced pressure. To the residue was added THF (3 mL). The reaction mixture was added dropwise to a mixture of 1-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)phenyl)methanamine (732 mg), TEA (646 mg) and dichloromethane (8 mL) at 0C over 10 min, and the reaction mixture was stirred at the same temperature for 2 hr. The reaction mixture was diluted with water, and the aqueous layer was extracted with dichloromethane. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (198 mg) . MS: [M+H]+ 360.1.

The synthetic route of 34415-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; HIRAYAMA, Takaharu; HIRATA, Yasuhiro; TOMINARI, Yusuke; IWAMURA, Naoki; SASAKI, Yusuke; ASANO, Moriteru; TAKAGI, Terufumi; OKANIWA,Masanori; YOSHIDA, Masato; ICHIKAWA, Takashi; IMAMURA, Shinichi; (113 pag.)EP3514149; (2019); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 213745-17-6, 4-Chloro-7-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine, 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, SDS of cas: 213745-17-6, blongs to pyrimidines compound. SDS of cas: 213745-17-6

To a pressure tube with dioxane (5 mL) was added 4-Chloro-7-cyclopentyl-5-iodo-7H- pyrrolo [2, 3-D] PYRIMIDINE, then ammonia hydroxide (5 mL). The pressure tube was sealed and heated at 120C overnight. All solvents were removed via reduced pressure, and the residue were purified through flash COLUMN (METHYLENE CHLORIDE/METHANOL : 97/3). The product was obtained as a white solid (300 mg, 92%). MS: 329.1 (MH+); HPLC Rf: 5.018 min.; HPLC purity: 99%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,213745-17-6, 4-Chloro-7-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/56830; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5267-07-2, 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 5267-07-2, name is 5-Pyrimidineacetic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-bromobenzene-l ,2-diamine (10) (0.281g, 1.5mmol) , 2-(pyrimidin-5-yl)acetic acid (11) (0.207g, 1.5mmol), and HATU (0.741g, 1.95mmol) in DCM (50ml) was added triethylamine (0.63ml, 4.5mmol). The reaction mixture was stirred at room temperature overnight. The solution was washed with saturated sodium bicarbonate (50ml) and brine (50ml). The DCM solution was dried over sodium sulfate and concentrated. The residue was purified by automated column chromatography columned using DCM and methanol as eluents. Yield 0.4g, 87%. MS: m/z 306.9 (M+H+).

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 5267-07-2, 5-Pyrimidineacetic acid.

Reference:
Patent; ZALICUS PHARMACEUTICALS LTD.; PAJOUHESH, Hassan; HOLLAND, Richard; ZHANG, Lingyun; PAJOUHESH, Hossein; LAMONTAGNE, Jason; WHELAN, Brendan; WO2012/116440; (2012); A1;,
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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. 57401-76-0, name is Ethyl 2-aminopyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 57401-76-0

To a solution of ethyl 2-aminopyrimidine-5-carboxylate (0.200 g, 1.196 mmol) in DME (6 ml), a suspension of sodium 2-methylbutan-2-olate (0.527 g, 4.79 mmol) in DME (6 ml) was added drop wise stirring at room temperature under nitrogen. The resulting yellow suspension was stirred at the same temperature for 30 minutes and then cooled to -10C. Methanesulfonyl chloride (0.278 ml, 3.59 mmol) was added drop wise maintaining the temperature below – 5C. After 1.5 hours water (30 ml) was added and the mixture was extracted with ethyl acetate (20 ml x 3). The combined organic layers were dried over sodium sulfate and evaporated. The residue was triturated with MeOH and the mother liquors were evaporated and triturated with EtOH. The two portions collected by filtration were mixed affording 0.152 g of a mixture of ethyl 2-(methylsulfonamido)pyrimidine-5-carboxylate and methyl 2-(methylsulfonamido)pyrimidine-5-carboxylate (about 1 : 1 ratio). This mixture was suspended in THF (6.380 ml) and 3N NaOH (0.425 ml, 1.276 mmol) was added. The resulting solution was heated to 50C for 2.5 hours. THF was evaporated and the aqueous solution was diluted with water (2 ml) and acidified with 6N HC1 (pH = 2) stirring at room temperature. The obtained precipitate was collected by filtration affording 2-(methylsulfonamido)pyrimidine-5-carboxylic acid as a white solid (0.133 g, 0.612 mmol, 51.1% yield, MS/ESI+ 218.0 [MH] +).

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, 57401-76-0, Ethyl 2-aminopyrimidine-5-carboxylate.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ARMANI, Elisabetta; AMARI, Gabriele; CAPALDI, Carmelida; ESPOSITO, Oriana; PERETTO, Ilaria; WO2013/45280; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia