Day: September 17, 2021

Application of 51421-99-9, 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.51421-99-9, name is 4-Chloro-2-methoxypyrimidine, molecular formula is C5H5ClN2O, molecular weight is 144.559, as common compound, the synthetic route is as follows.

To a stirred solution of 4-chloro-2-methoxypyrimidine (5.7 g, 39.4 mmol) in EtOH (100 mL)under Ar was added hydrazine hydrate (3.83 mL, 79 mmol) and the reaction mixture washeated up and stirred at 85C for 1 hr. Volatiles were removed under reduced pressure and the resulting crude material was purified by silica gel column chromatography (CH2CI2/MeOH/1- 5%/NH3 1%) to afford the title product (4.40 g, 31.4 mmol, 80% yield) as white solid. ESl-MS:141 [M+H] (LC-MS 2); R = 0.47 (CH2CI2/MeOH 9:1).

The chemical industry reduces the impact on the environment during synthesis 51421-99-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BLANK, Jutta; BORDAS, Vincent; COTESTA, Simona; GUAGNANO, Vito; RUEEGER, Heinrich; VAUPEL, Andrea; WO2014/191896; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1192711-37-7, 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 1192711-37-7 as follows.

Carboxylic acid 1.6 (3.15g, 15 mmol) was dissolved in N ,N- dimethylformamide (70 mL) and treated with HOBt (3.13g, 23 mmol) and EDC (4.4g, 23 mmol). After stirring ca. 25 min ammonia (0.5 M in 1,4-dioxane, 72 mL, 36 mmol) was added and the reaction stirred overnight. The following morning the reaction was diluted with water to a total volume of 500 mL and the desired product collected by filtration affording 3.62g (74%) of a light-beige solid. 1H NMR (DMSO-d6, 400 MHz): delta 9.30 (d, IH), 8.54 (s, IH), 8.15 (d, IH), 8.09 (s, IH), 7.74 (d, IH), 7.64 (m, 2H), 7.51 (t, IH), 3.77 (m, IH), 1.79 (m, 2H), 1.74 (m, 2H), 1.53 (m, IH), 1.41 (m, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1192711-37-7, its application will become more common.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; WO2009/131687; (2009); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 108381-28-8 ,Some common heterocyclic compound, 108381-28-8, molecular formula is C11H9ClN2O, 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.

First Step 2.6 g of 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenol and 1.7 g of 4-benzyloxy-2-chloropyrimidine were dissolved in 20 ml of N,N-dimethylformamide, to this solution was added 1.07 g of potassium carbonate, and the mixture was stirred for 2 hours at 80 C. The reaction solution was cooled to room temperature, then, this reaction solution was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with 10% aqueous sodium hydroxide solution, dried over anhydrous magnesium sulfate, and concentrated to obtain 1.6 g of 4-benzyloxy-2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}pyrimidine.

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. 108381-28-8, 4-(Benzyloxy)-2-chloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical Company, Limited; US6537948; (2003); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 18740-38-0, 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 18740-38-0 as follows.

EXAMPLE 402,4-Dichlorothieno[2,3-d]pyrimidine; The dione of Example 39 (2.6 g) was placed into a pressure vessel with phosphorus oxychloride (15 mL). The mixture was heated at 200 0C for 2.3 hours and then cooled to room temperature and concentrated under reduced pressure. Residual phosphorus oxychloride was azeotroped . twice with toluene (30 mL) under reduced pressure. The residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The resulting layers were separated and the organic layer was filtered through anhydrous magnesium sulfate and concentrated to dryness under reduced pressure to give 1.06 g of the title compound: MS (ESI+) for C6H2N2CI2S m/z205.0 (M+H)+. 1H NMR (400 MHz, CDCI3) delta 7.42 (d,1 H), 7.61 (d,1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18740-38-0, its application will become more common.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY LLC; WO2006/79916; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 111196-81-7, name is 2-Chloro-5-ethylpyrimidine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Chloro-5-ethylpyrimidine

3-Hydroxypropylamine (5.62 mL, 73.5 mmol, 1.2 equiv. ) was dissolved in 250 mL of TMOF/MEOH (1: 5) (TMOF = TRIMETHYL ORTHOFORMATE) and then 2,4- bis (trifluoromethyl) benzaldehyde (14.83g, 61.2 mmol, 1.0 equiv. ) was added to this solution at room temperature with stirring. The resulting solution was stirred at rt for 6 hours and then cooled to 0C. NaBH4 was added to the cooled reaction solution in portions with vigorous stirring. After TLC indicated the reduction complete, the reaction mixture was concentrated under reduced pressure. The residue was diluted with 250 mL of ethyl acetate and washed with water, brine and then dried over NA2SO4. After removal of solvent, 17.1 g (93% yield) colorless oil was obtained as desired N-2,5- bis (trifluoromethyl) benzyl-3-hydroxypropylamine (1C). H NMR (400 MHz, CDCL3), 8 (ppm): 7.9 (s, 1H), 7.75 (M, 2H), 4.0 (s, 2H), 3.8 (t, 2H), 2.85 (t, 2H), 1.76 (M, 2H). To a high pressure flask was added intermediate (1C) (12.23g, 40.6 mmol, 1.0 equiv. ), 2-chloro-5-ethylpyrimidine (4.9 mL, 40.6 mmol, 1.0 equiv. ), triethylamine (11.3 mL, 81.2 mmol, 2.0 equiv. ) and 50 mL of toluene. After the flask was sealed, it was heated to 180C with stirring. After reaction at same temperature for 48 hours, the reaction mixture was cooled to room temperature and then diluted with 100 mL of ethyl acetate. The resulting solution was washed with water, brine and the dried over NA2S04.- After removal of solvent, the residue was purified by chromatography to give 7.7 g (46% yield) of product (LE) as bright brown SOLID. H NMR (400 MHz, CDC13), 8 (ppm): 8. 15 (s, 2H), 7.90 (s, 1H), 7.67 (d, 1H) 9 7.30 (d, 1H), 5.02 (s, 2H), 3.71 (m, 2H), 3.53 (m, 2H), 2.42 (Q, 2H), 1.75 (M, 2H), 1.15 (T, 3H).

The synthetic route of 111196-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; WO2004/92130; (2004); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 131860-97-4, 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.131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, molecular formula is C15H13ClN2O4, molecular weight is 320.73, as common compound, the synthetic route is as follows.

Methyl (£)-2-{2-[6-chloropyiimidin-4-yloxy]phenyl}-3-methoxyacrylate (E) (3g of 95.4% strength) was charged to the reaction tube followed by the solvent (10 ml) then 2- cyanophenol (1.2g), base (1.5 mol equivalents) and the compound being tested as a catalyst (15 mol%). The reaction mixtures were held, with stirring, at 400C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for formation of product, throughout the hold period, by Gas Chromatography. Results are recorded as area % levels of methyl (£)-2-{2-[6- chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (II) and methyl (E)-2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE l The results are shown in Table 2 below:TABLE 2; Further screening experiments, using DMF as a solvent, were carried out as detailed below: Methyl (£)-2-{2-[6-chlororhoyrimidin-4-yloxy]ph.enyl}-3-methoxyacrylate (H) (6.4g of 45.2% strength solution in DMF) was charged to the reaction tube followed by further DMF (6.4 g), 2-cyanophenol (1.2g), potassium carbonate (1.5 mol equivalents) and the compound being tested as a catalyst (10 mol%). The reaction mixtures were held, with stirring, at 4O0C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for loss of starting material and formation of product, throughout the hold periods, by Gas Chromatography. Results are recorded as area % levels of methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3- methoxyacrylate (II) and methyl (2s)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3- methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE 3The results are shown in Table 4 below:

The chemical industry reduces the impact on the environment during synthesis 131860-97-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43977; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3177-24-0, 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. 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below.

Example 287: Preparation of 4-(cyclopropylamino)-2-((2-oxo-l,2,3,4-tetrahydroquinolin-6- yl)amino)pyrimidine-5-carbonitrile and 2-(cyclopropylamino)-4-((2-oxo-l,2,3>4- tetrahydroquinolin-6-yl)amino)pyrimidine-5-carbonitrile.2,4-Dichloropyrimidine-5-carbonitrile (0.100 g, 0.575 mmol), cyclopropanamine (0.040 ml, 0.575 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.1 10 ml, 0.632 mmol) were mixed in acetonitrile (2 ml). The mixture was microwaved at 70 °C for 10 min and then concentrated. 6- amino-3,4-dihydroquinolin-2(l H)-one (0.093 g, 0.575 mmol) and acetic acid (0.035 g, 0.575 mmol) were added. The mixture was microwaved at 1 10 °C for 20 min and then concentrated. 14 mg of 4-(cyclopropylamino)-2-((2-oxo- l ,2,3,4-tetrahydroquinolin-6-yl)amino)pyrimidine-5- carbonitrile and 14 mg of 2-(cyclopropylamino)-4-((2-oxo-l ,2,3,4-tetrahydroquinolin-6- yl)amino)pyrimidine-5-carbonitrile were recovered after automated reverse phasechromatography (water-MeCN). MS calcd for [Ci7Hi6N60+H]+: 321.15 found 321.00.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3177-24-0, its application will become more common.

Reference:
Patent; SALK INSTITUTE FOR BIOLOGICAL STUDIES; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; YALE UNIVERSITY; SHAW, Reuben J.; EGAN, Daniel F.; COSFORD, Nicholas; TURK, Benjamin; VAMOS, Mitchell; PANICKAR, Dhanya Raveendra; CHUN, Matthew; SHEFFLER, Doug; (315 pag.)WO2016/33100; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 17573-78-3, 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.17573-78-3, name is 4,5,6-Trifluoropyrimidine, molecular formula is C4HF3N2, molecular weight is 134.06, as common compound, the synthetic route is as follows.

Example (IV-1) Process e) 2.52 g (0.01 mol) of (5,6-dihydro-[1,4,2]oxathiazin-3-yl)-(2-hydroxyphenyl)-methanone O-methyloxime are dissolved in 10 ml of acetonitrile and admixed with 1.7 g (0.0123 mol) of potassium carbonate. The mixture is then cooled with stirring to 0 C., and 1.34 g (0.01 mol) of 4,5,6-trifluoropyrimidine are then added. Without further cooling, the mixture is stirred for another 12 hours. The solvent is then distilled off under reduced pressure and the residue is poured into water and extracted with ethyl acetate. The organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 2.3 g (62% of theory) of [2-(5,6-difluoro-pyrimidine-4-yloxy)-phenyl]-(5,6-dihydro-[1,4,2]oxathiazin-3-yl)-methanone O-methyloxime. 1H NMR spectrum (CDCl3/TMS): delta=3.15/3.16/3.17/3.18 (2H); 3.83 (3H); 4.11/4.12/4.13/4.14 (2H); 7.26-7.53 (4H); 8.20 (1H) ppm.

The chemical industry reduces the impact on the environment during synthesis 17573-78-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bayer Aktiengesellschaft; US6407097; (2002); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-66-9, Adding some certain compound to certain chemical reactions, such as: 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide,molecular formula is C5H4ClN3O, 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 22536-66-9.

Methyl (2-(methylamino)ethyl)carbamic acid tert-butyl ester (1.88 g, 9.99 mmol), 2-chloropyrimidine-4-carboxamide (1.73 g, 10.98 mmol) and potassium carbonate under nitrogen. (1.52g, 10.98mmol) was added toN,N-dimethylformamide (15 mL).The reaction mixture was warmed to 130 C, stirred for 20 hr then cooled to room temperature, filtered and evaporated. The resulting residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 1/1) to afford the title compound as a white solid (2.50g, 81.0%).

According to the analysis of related databases, 22536-66-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Xu Xianjie; Zhang Yingjun; Zheng Changchun; (42 pag.)CN105085491; (2019); B;,
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. 14080-23-0, name is 2-Cyanopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 14080-23-0

[0505] Synthesis of methyl pyrimidine-2-carboxylate:[0506] To a stirred solution of pyrimidine-2-carbonitrile (12.0 g, 114.28 mmol) in MeOH (20 mL) was added methanolic HC1 (180 mL) at 0 C and stirred for 16 h. After completion of starting material by TLC, the volatiles were evaporated under reduced pressure. The residue was neutralized with saturated NaHC03 solution and extracted with EtOAc. The combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was triturated with Hexane to afford methyl pyrimidine-2-carboxylate (10.0 g, crude) as yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 9.08 (d, 2H), 7.76 (t, 1H), 3.92 (s, 3H); LC-MS: 94.32%; 139 (M++l) (column; Chromolith RP-18, (100×4.6 mm); RT 2.85 min. 5mM NH4OAc: ACN; 0.8 ml/min); TLC: 70% EtOAc/Hexane (Rf: 0.2).

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, 14080-23-0, 2-Cyanopyrimidine.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia