Day: October 22, 2020

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. 125401-75-4, name is 2,6-Bis((4,6-dimethoxypyrimidin-2-yl)oxy)benzoic acid. This compound has unique chemical properties. The synthetic route is as follows. 125401-75-4

EXAMPLE 1 Preparation of 1-ethoxycarbonyloxyethyl 2,6-bis[(4,6-dimethoxypyrimidin -2-yl)oxy]benzoate (Compound No. 5) 1.7 g (4.0 mmol) of 2,6-bis[(4,6-dimethoxypyrimidin-2-yl) oxy]benzoic acid and 0.2 g of 60% sodium hydride were dissolved in N,N-dimethylformamide. After the generation of hydrogen ceased, 0.68 g (4.4 mmol) of 1-chloroethylethylcarbonate was added to the solution and the resultant mixture was reacted at 100 C. for 1 hour. After completing the reaction, the reaction mixture was added to ice water and was extracted with ethyl acetate. The ethyl acetate layer was dried with anhydrous sodium sulfate, and the ethyl acetate was distilled off. The residue was purified by silica gel column chromatography, and ethanol/hexane were added thereto to precipitate a solid, which was then filtered out to obtain 1.4 g of a white crystal having a melting point of from 97 to 100 C.

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, 125401-75-4, 2,6-Bis((4,6-dimethoxypyrimidin-2-yl)oxy)benzoic acid.

Reference:
Patent; Kumiai Chemical Industry Co. Ltd.; Ihara Chemical Industry Co., Ltd.; US5154750; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

1820-81-1 , The common heterocyclic compound, 1820-81-1, name is 5-Chlorouracil, molecular formula is C4H3ClN2O2, 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.

5-chlorouracil (100 g, 99% content; 0.68 mol), triphenylphosphine oxide (59.6 g, 98% content; ie 0.21 mol) and nitrobenzene (150 ml) in a 250 ml belt In a three-necked flask equipped with a thermometer, a stirrer, an air tube, and a condenser (-5 – 10 C),The system uses nitrogen to check for leaks. The mixture of 5-uracil is heated to 80 C,Phosgene (340 g, 99% content; ie 3.4 mol) was passed through the gas pipe through the reaction liquid.A small amount of phosgene begins to reflux during the addition. The phosgene access time is 20 minutes.The mixture was heated to 125 C. When the temperature is 110 C, a large amount of gas is released.At the same time, the phosgene of the condenser is largely returned After 30 minutes, the reaction mixture was taken to a clear red color. The deflation rate after 40 minutes was very slow; the reaction solution was sampled and then the reaction was continued for 1 hour, during which time all deflation had stopped. HPLC analysis indicated complete reaction. The reaction mixture was cooled and unreacted phosgene was removed by purging with nitrogen. The column was packed, the solvent was recovered under reduced pressure, and the product was further distilled to obtain 116.0 g of a product of 99% or more, and the yield was about 93.0%.

According to the analysis of related databases, 1820-81-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hangzhou Bulang Bio-pharmaceutical Technology Co., Ltd.; Huang Guoxiang; Ma Xiaoke; (6 pag.)CN109516958; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
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.5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, molecular weight is 183.4231, as common compound, the synthetic route is as follows.5750-76-5

General procedure: To a solution of compound 15 (37.65 mmol) in 1,4-dioxane (50 mL) were added diisopropylethylamine (7.3 g, 56.48 mmol) and 2,4,5-trichloropyrimidine (6.9 g, 37.65 mmol) or 2,4-dichloro-5-fluoropyrimidine (6.3 g, 37.65 mmol). The reaction was heated to 60 C and stirred for 2 h. After being cooled to room temperature, the reaction mixture was added to water (300 mL). The precipitate was filtered, and the filtered cake was rinsed with additional cool water and dried in a vacuum oven to give the compound 16a,b (91%), which was used without further purification.

Statistics shows that 5750-76-5 is playing an increasingly important role. we look forward to future research findings about 2,4,5-Trichloropyrimidine.

Reference:
Article; Ge, Yang; Yang, Haijun; Wang, Changyuan; Meng, Qiang; Li, Lei; Sun, Huijun; Zhen, Yuhong; Liu, Kexin; Li, Yanxia; Ma, Xiaodong; Bioorganic and Medicinal Chemistry; vol. 25; 2; (2017); p. 765 – 772;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

36315-01-2, 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 36315-01-2 as follows.

24.5g carbamate, 11.8g 4,6-dimethoxy-2-pyrimidinamine, 200mL tolueneMix and put into the reaction vessel and heat to reflux. After about 0.5h, start to collect the mixed solution of toluene and ethanol.Fresh toluene was added at the same speed, and the reaction was completed after refluxing for 5h. Stop adding toluene, distill off some toluene, cool to room temperature, and filter.After drying, 24.6 g of nicosulfuron was obtained, the mass fraction was 95.0%, and the yield was 75.6%.

The chemical industry reduces the impact on the environment during synthesis 36315-01-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Heilongjiang Suihua Farming Chenhuan Biological Preparation Co., Ltd.; Du Chuanyu; Zhao Mingxin; Jiang Yushan; Zhou Dewei; Wang Weisheng; (7 pag.)CN111269214; (2020); A;,
Pyrimidine | C4H4N2 – PubChem,
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.4212-49-1, name is 5-Ethyluracil, molecular formula is C6H8N2O2, molecular weight is 140.14, as common compound, the synthetic route is as follows.4212-49-1

Step A: Synthesis of 2,4-dichloro-5-ethylpyrimidine. To a suspension of 5-ethyluracil (1 g, 7.1 mmol) in POCl3 (4.5 mL) was slowly added N,N-dimethylaniline (1 mL). The reaction was heated at reflux (~120 C) for 5 h until the starting material was completely dissolved and the entire solution turned a purple color. The mixture was allowed to cool and poured very slowly into ice (~40 g). The resulting ppt was filtered and washed with ice water. The ppt was dissolved with a minimal amount of DCM and poured onto a short column of silica gel, and the product (1.2 g, ~ 100 %) was obtained by column chromatography with DCM. 1H NMR (400 MHz, CDCl3) delta 8.42 (s, 1 H), 2.75 (q, 2 H, J = 7.6 Hz), 1.29 (t, 3 H, J = 7.6 Hz).

Statistics shows that 4212-49-1 is playing an increasingly important role. we look forward to future research findings about 5-Ethyluracil.

Reference:
Patent; Taisho Pharmaceutical Co. Ltd.; Arena Pharmaceuticals, Inc.; EP1464335; (2004); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

1722-12-9, 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. 1722-12-9, name is 2-Chloropyrimidine, molecular formula is C4H3ClN2, 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.

Example 1; Pd(PPh3VNaHCO3DME/H,O/reflux [00203] 2,2-Dimethyl-N-(2-pyrimidin-2-yI-phenyI)-propionamide: A 5 L flask was charged with the above depicted boronic acid as a tetrahydrate (281.4 grams, 960 mmoles), 2- chloropyrimidine (100 g, 874 mmoles), NaHCO3 (146.8 grams, 1.746 moles), and Pd(PPh3)4 (10.0 grams, 8.72 mmoles). Water (IL) and dimethoxyethane (IL) were added, and the mixture was heated slowly to 83 0C (internal temperature) over a 1 hour period with overhead stirring. After ~2 hours all solids had dissolved. The reaction was allowed to stir for 8 hours. The mixture was cooled to room temperature and stirred overnight after which time a thick precipitate had formed. The crude mixture was diluted with water (2L) and stirred for an additional 2 hours after which time the mixture was filtered and the solids were washed sequentially with water, 0.1 N NaOH, and water again. The solids were then dried under high vacuum at 50 0C to afford the title compound (-233 grams) as a tan powder.

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. 1722-12-9, 2-Chloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/56330; (2007); A1;,
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 145783-14-8, name is 4,6-Dichloro-5-nitro-2-(propylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. 145783-14-8

Example 3. Preparation of l-^SaR^S^R^aSV-ftS-Amino–chloro-l- phiropylthioJpyrimidin-^yllaminoJ-ljl-dimethyltetrahydro-SaH- cyclopenta[ 99%). The catalyst was filtered off and washed with methyl-tert-butylether (117 kg). The hydrogenation was repeated with a second portion of 4,6-Dichloro-5-nitro-2-(propylthio)pyrimidine (71 kg). The two hydrogenation solutions were combined. Water was separated off and the organic layer was distilled under reduced pressure and at a jacket temperature of 300C. To the resulting brown oil ethylene glycol (221 kg) was charged and the distillation was continued until no more methyl-tert-butylether was distilling off.

Statistics shows that 145783-14-8 is playing an increasingly important role. we look forward to future research findings about 4,6-Dichloro-5-nitro-2-(propylthio)pyrimidine.

Reference:
Patent; ASTRAZENECA AB; AUFDENBLATTEN, Rhony; BOHLIN, Martin, Hans; HELLSTROeM, Helena; JOHANSSON, Peter, W; LARSSON, Ulf, G; RECKNAGEL, Mikaela; WEISS, Ursula, heiress of WEISS Andreas (Deceased); WO2010/30224; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

156-81-0, 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. 156-81-0, name is Pyrimidine-2,4-diamine, the common compound, a new synthetic route is introduced below.

A solution of 2-bromo-1-(5-chloro-2,4-dimethoxyphenyl)ethanone 3 (140 mg, 0.47 mmol) and pyrimidine-2,4-diamine (50 mg, 0.45 mmol) in acetone (5 mL) was heated to reflux for 16 h. The reaction mixture was cooled to room temperature. The precipitate was filtered and treated with dilute ammonia. Precipitate was filtered, washed with water, and dried under reduced pressure to yield 2-(5-chloro-2,4- dimethoxyphenyl)imidazo[l,2-a]pyrimidin-7-amine 158b ( 95 mg, 36%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta 8.36 (d, 1H J = 7.2Hz), 8.09 (s, 1H). 7.76 (s, IH), 6.84 (s, IH), 6.76 (s, 2H), 6.22 (d, 1H, J = 7.2Hz), 3.98 (s, 3H), 3.92 (s, 3H); ESI MS m/z 305 [M+H]+

Statistics shows that 156-81-0 is playing an increasingly important role. we look forward to future research findings about Pyrimidine-2,4-diamine.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

705-24-8, 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 705-24-8 as follows.

To a solution of 1 -methylpiperidin-4-ol (35 mg, 0.30 mmol) in THF (0.5 mL) at 0C was added 60% NaH (12 mg, 0.30 mmol). After the mixture was stirred for 20 minutes, a solution of Intermediate 2 (42 mg, 0.10 mmol) in THF (0.5 mL) was added. Then the ice bath was removed, and the reaction mixture was stirred at room temperature for two hours. The reaction was quenched by water (0.1 mL), and concentrated. The residue was purified directly by MS-HPLC to afford Compound 39 (18 mg, 35%). LCMS (method A): m/z 503.4 (M+H)+. ‘H NMR (CDCI3) delta 8.50 (s, 1H), 77.44 (d, 2H), 7.17 (d, 2H), 5.72 (d, 1H), 5.31 (m, 1H), 4.60 (br, 1H), 3.60 (m, 1H), 3.40 (m, 2H), 3.24 (br, 1H), 3.03 (br, 2H), 2.92-2.77 (m, 4H), 2.40 (br, 1H), 2.25 (m, 3H), 2.1 1-1.88 (m,4H); Following procedure as described in Example 2, and replacing THF with DMF, piperidine-2,4-dione (249 mg, 2.20 mmol) was converted to Compound 3A. The crude material was purified by silica gel chromatography (0-90% EA/hexane) to afford Compound 3A (375 mg, 64%). LCMS (method A): m/z 294.3 (M+H)+. XH NMR (CDC13): delta 7.14 (s, 1H), 5.97 (br s, 1H), 5.83 (s, 1H), 3.60 (t, 2H), 2.72 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,705-24-8, its application will become more common.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; MCGUINNESS, Brian F; XU, Xiaoqing; KULTGEN, Steven G.; MCMASTER, Ellen Sieber; BEASLEY, James R.; (356 pag.)WO2018/5794; (2018); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

588-36-3, 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. 588-36-3, name is 4-Amino-5-hydroxymethyl-2-(methylthio)pyrimidine. A new synthetic method of this compound is introduced below.

To a solution of (4-amino-2-(methylthio)pyrimidin-5 -yl)methanol (11 g, 63 mmol, 1.0 equiv) in CHC13 (900 mL) was added Mn02 (43.85 g, 504 mmol, 8.0 equiv). The suspension was stirred overnight at rt. The resulting mixture was filtration and washing with CHC13. The filtrate was concentrated under vacuum to give 10 g (94%) of 4-amino-2-(methylthio)pyrimidine-5- carbaldehyde as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,588-36-3, 4-Amino-5-hydroxymethyl-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PRINCIPIA BIOPHARMA, INC.; VERNER, Erik; BRAMELD, Kenneth Albert; WO2015/120049; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia