Day: May 18, 2021

Synthetic Route of 13162-26-0, 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. 13162-26-0, name is 2,4-Dichloro-6-methyl-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

Step A: 4-(4-bromo-2,6-dimethylphenoxy)-2-chloro-6-methyl-5-nitropyrimidine; A solution of LiHMDS in THF (1M, 77 ml, 77 mmol) was added at -78 C. to a mixture of 2,6-dimethoxy-4-bromophenol (14.07 g, 70 mmol) in THF (100 ml) over 15 minutes. The mixture was stirred for an additional 2 hours. Phenoxide salt was observed as solid suspension. The mixture was cooled with liquid nitrogen to a temperature around -100 C. and then a solution of 2,6-dichloro-4-methyl-5-nitropyrimidine (17.47 g, 84 mmol) in THF (50 ml) was added rapidly to the mixture, which turned dark red. The reaction was kept at a temperature around -100 C. for 1 hour. After warming to room temperature, the mixture was filtered and the solid was washed with ethanol to yield 16.75 g of the title product. The filtrate was concentrated and crystallized to obtain an additional 5.60 giving a total amount of 22.35 g of desired compound (60 mmol, 85%). 1H NMR (CDCl3, 400 MHz) delta 2.11 (s, 6H), 2.63 (s, 3H), 7.27 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13162-26-0, 2,4-Dichloro-6-methyl-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Ardea Biosciences; US2009/162319; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 89793-12-4 , The common heterocyclic compound, 89793-12-4, name is Ethyl 2-chloropyrimidine-5-carboxylate, molecular formula is C7H7ClN2O2, 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.

Synthesis of Intermediate 4: Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 min. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95 °C for 4 hrs. The solution was allowed to slowly cool to r.t. This solution was poured onto H20 (20 L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50 °C for 24 hr., yielding 896 g of compound 4 (solid, 86.8percent).

The synthetic route of 89793-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACETYLON PHARMACEUTICALS, INC.; VIB VZW; KATHOLIEKE UNVERSITEIT LEUVEN; LIFE SCIENCES RESEARCH PARTNERS VZW; JARPE, Matthew, Blaire; BENOY, Veronick; HELLEPUTTE, Lawrence, Van; VAN DEN BOSCH, Ludo; (50 pag.)WO2016/90230; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 14160-93-1 ,Some common heterocyclic compound, 14160-93-1, molecular formula is C5H4ClN3O, 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.

A solution of 4-amino-6-chloropyrimidine-5-carbaldehyde (F1) (7.62 mmol, 1.2 g) was dissolved in a mixture of 25 ml of glacial acetic acid and 4 ml of water,Methoxyamine hydrochloride (13.71 mmol, 1.14 g) was added,The reaction was carried out at 25 C overnight.After completion of the reaction, 20 ml of water was added to the reaction mixture, and the mixture was extracted with 50 ml of ethyl acetate. The organic layer was washed with water 3 times, 10% sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, The solvent was distilled off and purified by column chromatography (eluent petroleum ether: ethyl acetate = 3: 1) to give a white solid in 99% yield.

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. 14160-93-1, 4-Amino-6-chloropyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shan Dong University; Zhao, Guisen; Lu, Jinjie; Wang, Guanjie; Yang, Dezhi; Zhang, Zhen; Jing, Yongkui; (32 pag.)CN106045918; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3680-69-1, Adding some certain compound to certain chemical reactions, such as: 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H4ClN3, 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 3680-69-1.

4-chloro-7H-pyrrolo2,3-dipyrimidine (2-E, 20.0g, 130.7mmol) dissolved in DCM (800 mL) was treated portion-wise with N-bromosuccinimide (26.7 g. 149.8 mmol), while maintaining the temperature around 25-30C. The reaction mixture was stirred at room temperature overnight. Water was added (500 mL) and the phases were separated. The organic phase was dried over NaSO4, filtered and concentrated in vacuo. The crude product was triturated in Et2O affording after filtration 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine as a white solid (2-F, 22.43 g, 74%).

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. 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARQULE, INC.; LAPIERRE, JEAN-MARC; EATHIRAJ, SUDHARSHAN; NAMDEV, NIVEDITA; SCHWARTZ, BRIAN; OTA, YUSUKE; MOMOSE, TAKAYUKI; TSUNEMI, TOMOYUKI; INAGAKI, HIROAKI; NAKAYAMA, KIYOSHI; (67 pag.)TW2017/22956; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference 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 (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate (97.6 gm), 2-cyanophenol (36.9 gm), and potassium carbonate (25.4 gm) are added to, mixed, and dissolved in an aprotic solvent (241 gm) at room temperature. In this embodiment, the aprotic solvent is, for example, toluene. Then, 1-methylpyrrolidine (10.2 gm, 0.4 eq) is added as a catalyst, and stirred until uniform to form a basic mixture. Subsequently, the basic mixture is heated to 80 C., and reacted for 3 hrs. (0019) The basic mixture after reaction is subjected to a first distillation under a reduced pressure of 100 torr at 80 C., and the product left after the first distillation under reduced pressure is azoxystrobin. The distillate by the first distillation under reduced pressure is detected by gas chromatography (GC), and 1-methylpyrrolidine is determined to have a recovery rate of 96.3%. (0020) Azoxystrobin left after the first distillation under reduced pressure is added to the aprotic solvent (241 gm) and water (114 gm), mixed, and stirred until azoxystrobin is completely dissolved. After standing for layer separation, an upper first organic layer is collected, and then a lower aqueous layer is collected and further added with the aprotic solvent (15 gm). Next, an upper second organic layer is collected. The first organic layer and the second organic layer are combined, and detected by high performance liquid chromatography (HPLC) to show a yield of azoxystrobin of 94.9%. The combined organic layer is subjected to a second distillation under reduced pressure at 50-60 C. under 20-40 torr, to remove the solvent. This gives a crude product. The crude product is dissolved in methanol (156 gm) at 60 C., cooled to normal temperature and then to 5 C., and filtered to obtain a crystalline solid. The crystalline solid was washed with methanol (13 gm) and then dried at 50 C., to obtain purified azoxystrobin (112.9 gm) as a solid (yield 91.5%).

Statistics shows that 131860-97-4 is playing an increasingly important role. we look forward to future research findings about (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate.

Reference:
Patent; SINON CORPORATION; CHEN, Chien-Hsing; HSIEH, Ming-Fang; LIN, Chih-Da; LIU, Chien-Yu; (4 pag.)US2020/165210; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 347418-42-2, 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 347418-42-2 as follows.

Step 2 17.5 g Sodium hydride (60% dispersion in mineral oil) was suspended in300 ml N,N-dimethylformamide. The reaction mixture was cooled with an ice- water bath. 70.0 ml Diethyl malonate was added dropwise over 45 minutes. The resulting clear mixture was stirred at ambient temperature for 30 minutes. 36.2 g Crude product from the preceded step was added dropwise over 20 minutes at ambient temperature. The orange reaction mixture was stirred at ambient temperature. Reaction progress was monitored with HPLC. After 18 hours, the reaction mixture was concentrated in vacuo to remove most of the N,N- dimethylformamide.300 ml diethyl ether and100 ml water were added and the mixture was stirred vigorously for 5 minutes. The pH of the mixture was adjusted to ~7 with aqueous hydrochloric acid (1.5 M). The layers were separated and150 ml diethyl ether was added to the aqueous layer. The pH was again adjusted to ~7. The combined organic layers were washed with300 ml brine, dried (Na2S04) and concentrated in vacuo. The obtained yellow oily liquid contained still some mineral oil (floating on top). Most of the mineral oil was removed by using a separation funnel. The excess of diethyl malonate still present was removed by vacuum distillation (80C, 0.65 mbar). The product diethyl (5- fluoro-4-pyrimidinyl)malonate was isolated as a yellow oily liquid (89.6% purity acc. HPLC, NMR confirms expected structure) that was used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,347418-42-2, its application will become more common.

Reference:
Patent; SYNTHRON B.V.; OVEREEM, Arjanne; ZHU, Jie; WO2011/110198; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 504-17-6 ,Some common heterocyclic compound, 504-17-6, molecular formula is C4H4N2O2S, 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.

General procedure: A mixture of an aldehyde (0.25mmol), 2-thiobarbituric acid (0.5mmol), ammonium acetate (0.3mmol) and CuFe2O4 (10mol%) were added in distilled H2O. Then, ultrasonic probe was directly immersed in the resulting mixture. After completion of the reaction (TLC), the solvent was evaporated and the precipitate was washed from ethanol and hot water to afford the pure product. All products were identified by physical and spectroscopic data.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,504-17-6, its application will become more common.

Reference:
Article; Naeimi, Hossein; Didar, Asieh; Ultrasonics Sonochemistry; vol. 34; (2017); p. 889 – 895;,
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.130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, molecular formula is C11H15ClN2O2, molecular weight is 242.7, as common compound, the synthetic route is as follows.HPLC of Formula: C11H15ClN2O2

300 ml of acetonitrile was charged followed by 20.0 g of 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido-[1,2-a]-pyrimidin-4-one and 21.0 g of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride at room temperature. The reaction mass was stirred at room temperature for 5 minutes and 20.0 g of potassium carbonate and 0.7 g of potassium iodide were charged. Further, 0.2 g of sodium borohydride was charged and the temperature was raised to 65±2 C. The reaction mass was maintained at 65±2 C. for 25 hours. After reaction completion, the reaction mass was slowly cooled to room temperature. The solids were filtered, washed with 50 ml of acetonitrile and then dissolved in 800 ml of methylene chloride at room temperature. The contents were heated to 30-35 C., maintained for 10 minutes, filtered and washed with 20 ml of methylene chloride. The clear filtrate was distilled completely under vacuum below 35 C. and replaced with 50 ml of acetone. Further, 300 ml of acetone was charged, heated to 45 C. and stirred for 30 minutes. The reaction mass was cooled to room temperature and stirred for 1 hour. The product was filtered, washed with 20 ml of acetone and dried under vacuum at 50-55 C. to yield paliperidone (30 g, yield: 150% w/w, efficiency: 85.11%, keto impurity by HPLC: 0.01%, total impurity level by HPLC: 1.0%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,130049-82-0, 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, and friends who are interested can also refer to it.

Reference:
Patent; CIPLA LIMITED; Puppala, Ravikumar; Pathi, Srinivas Laxminarayan; Kankan, Rajendra Narayanrao; US2014/200228; (2014); 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. 4595-60-2, name is 2-Bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Bromopyrimidine

General procedure: A Schlenk tube was charged with the prescribed amount of catalyst, aryl halide (1.0 mmol), 3-(hydroxymethyl)phenylboronicacid (1.5 mmol), TBAB (1.0 mmol), the selected base (3.0 mmol), and water under nitrogen atmosphere. The reaction mixture was heated at 100 C for 12 h. After cooling,the mixture was extracted with CH2Cl2, the solvent was evaporated,and the product was separated by passing through a silica gel column with CH2Cl2/ethyl acetate (5:1) aseluent. The products 2f, 2j, 2l, and 2o were new compounds and were determined by 1H and C13 NMR. Other products were characterized by comparison with data in the literature.

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, 4595-60-2, 2-Bromopyrimidine.

Reference:
Article; Gao, Hui; Xu, Chen; Li, Hong-Mei; Lou, Xin-Hua; Wang, Zhi-Qiang; Fu, Wei-Jun; Bulletin of the Korean Chemical Society; vol. 36; 9; (2015); p. 2355 – 2358;,
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. 213265-83-9, name is 4,6-Dichloro-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 4,6-Dichloro-5-fluoropyrimidine

Example 1.1: Preparation of 4-(l-(5-Ethylpyrimidin-2-yl)piperidin-4-yloxy)-5-fluoro-6-(2- methyl-6-(methylsulfonyl)pyridin-3-yloxy)pyrimidine (Compound 1).Step A: Preparation of tert-Butyl 4-(6-Chloro-5-fluoropyrimidin-4- yloxy)piperidine-l-carboxylate.To a solution of 4,6-dichloro-5-fluoropyrimidine (1.00 g, 5.99 mmol) and teri-butyl 4- hydroxypiperidine-1 -carboxylate (1.205 g, 5.99 mmol) in THF (10 mL) at -78 C was added 1 M potassium teri-butoxide solution in THF (5.99 mL, 5.99 mmol) dropwise. The mixture became thick and additional THF (10 mL) was slowly added. After stirring for 15 min, the mixture was diluted with water and extracted with EtOAc. The organic layer was concentrated under reduced pressure and purified by silica gel flash column chromatography to give the title compound as a colorless oil that slowly became a white solid (1.9561 g, 98%). Exact mass calculated for ^Eta19alphaRhoNu303: 331.1, found: LCMS m/z = 332.4 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.45 (s, 9H), 1.75-1.85 (m, 2H), 1.98-2.04 (m, 2H), 3.28-3.36 (m, 2H), 3.75-3.81 (m, 2H), 5.30-5.39 (m, 1H), 8.31 (s, 1H).

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, 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; WO2012/145604; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia