Day: May 25, 2021

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. 1032452-86-0, name is 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole. A new synthetic method of this compound is introduced below., category: pyrimidines

P-Toluenesulfonic acid hydrate (22.73 g, 119.5 mmol)Was added to a solution of 3- (2-chloropyrimidin-4-yl) -1-methyl-indole (Intermediate 20, 24.27 g, 99.58 mmol)And 4-fluoro-2-methoxy-5-nitroaniline (Intermediate 22, 18.54 g, 99.58 mmol)In a mixture of 2-pentanol (500 mL).The resulting mixture was stirred at 105 C for 2.5 hours.Then cooled to room temperature.The resulting precipitate was collected by filtration,Washed with 2-pentanol (50 mL), dried under vacuum,Some of the desired product was obtained as a yellow solid. The filtrate was cooled,The resulting precipitate was collected by filtration,Washed with 2-pentanol (10 mL).The two batches were combined and ground with CH? CN to obtain a solid,The solid was collected by filtration, dried under vacuum,The title compound was obtained as a yellow solid (37.4 g, 95%).

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, 1032452-86-0, 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole.

Reference:
Patent; Jiao Yuqi; (53 pag.)CN107043369; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 51940-64-8, Adding some certain compound to certain chemical reactions, such as: 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate,molecular formula is C7H6Cl2N2O2, 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 51940-64-8.

1.58 g (7.18 mmol) in ACN was added 920 mg (8.6 mmol) p-toluidine and ~2 mL DIE A. The reaction was stirred at room temperature for ~1 hour. The ACN was removed in vacuo until solid precipitated. At this point water (-50 mL) was added and the solid was filtered. The solid (B6.2) was dried and massed to be 1.85 g (89% yield). To 1.01 g (3.47 mmol) of B6.2 in a 50/50 mixture of THF/H20 was added 4.16 mmol of LiOH in H20 (1.2 eq). The reaction was stirred at room temperature for 30 minutes and then was acidified to pH~2 with 1 M HCl (aq). The volatiles were removed and the resulting solid was filtered to give 613 mg B6.2. To B6.2 in DMF was added 662 mg HOBt H20 and 708 mg EDC HCl. After stirring for 2 hours and additional 0.5 eq of EDC HCl was added. The reaction was stirred for 1 hour and then NH3 in dioxane (excess) was added. The reaction was stirred for 45 minutes and then the dioxane was removed in vacuo. Water was added which led to a precipitate. The solid (B6.3) was filtered, washed with water and dried. To -200 mg B6.3 in ~2 mL NMP and 0.3 mL DIEA was added 240 mg (S)-tert-butyl 1 -aminopropan-2-ylcarbamate. The reaction mixture was stirred at 90C for 2 hours and was then cooled. Water was added, solid precipitated and was filtered. Similar to Scheme 2 (example 73), a Boc-deprotection utilizing DCM/TFA afforded the title compound. MS found for C15H2ON6O as (M+H)+301.2.

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. 51940-64-8, Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong J.; KANE, Brian; XU, Qing; BAUER, Shawn M.; SONG, Yonghong; PANDEY, Anjali; DICK, Ryan; WO2013/78468; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1224944-77-7, 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 1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Into a 50 mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed a solution of ethyl 5-chloropyrazolo1,5-a]pyrimidine-3-carboxylate (300 mg, 1.33 mmol) in N,N-dimethylformamide (20 mL), tert-butyl N-(prop-2-yn-1-yl)carbamate (408 mg, 2.63 mmol), triethylamine (1.8 mL), copper (I) iodide (24 mg, 0.13 mmol), and Pd(PPh3)2Cl2 (47.1 mg, 0.07 mmol). The resulting mixture was stirred for 5 h at room temperature. After concentrated under vacuum, the residue was treated with 30 mL of ethyl acetate. The resulting mixture was washed with 3 x20 mL of water and 2 x 20 mL of sat. ammonium chloride. The organic phase was dried over sodium sulfate, concentrated, and filtered under reduced pressure. This resulted in ethyl 5-(3-[[(tert-butoxy)carbonyl]amino]prop-1-yn-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate as an oil.

According to the analysis of related databases, 1224944-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; CHILDERS, Matthew, L.; GIBEAU, Craig, R.; HO, Ginny Dai; TSUI, Honchung; (80 pag.)WO2016/144844; (2016); A1;,
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.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.Formula: C15H13ClN2O4

In this example, a trimethylamine solution in water with the amount of 15 mol % of methyl (E)-2-[2-[6-chloropy-rimidin-4-yloxy]phenyl]-3-methoxyacrylate was used as a catalyst to synthesize azoxystrobin. The specific preparation method was:150 g of toluene, 80.99 g (0.25 mol, 99%) of methyl (E)-2-[2-[6-chloropyrimidin-4-yloxy]phenyl]-3-methoxy-acrylate, 33.09 g (0.275 mol, 99%) of 2-cyanophenol, 27.88 g (0.2 mol, 99%) of potassium carbonate and 8.96 g (0.0375 mol, having a concentration of 33%) of trimethylamine solution in water were added sequentially into a 500 mL reaction flask, stirred, heated to 80 C. and incubated for 4h. When the reaction was completed, 100 g of water was added. Layers were separated to obtain 247.34 g of a toluene solution of azoxystrobin, with a content of 41.21% (w/w), which is 98.94% of the theoretical value.The post-processing was performed as Example 1 toprovide 98.92 g of azoxystrobin with a content of 98.43%and a yield of 96.55%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, and friends who are interested can also refer to it.

Reference:
Patent; CAC NANTONG CHEMICAL CO., LTD; Yang, Binglian; Wang, Haishui; Xie, Simian; Tian, Xiaohong; Xu, Jiwang; (8 pag.)US10189793; (2019); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 6153-44-2, Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate, 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, COA of Formula: C6H6N2O4, blongs to pyrimidines compound. COA of Formula: C6H6N2O4

To methyl 2,6-dioxo-l,2,3,6-tetrahydropyrimidine-4-carboxylate (900 mg, 5.29 mmol) was added DMF (17 mL). The mixture was cooled with an ice bath and lithium hydride (66.4 mg, 7.94 mmol) was then added in portions. The mixture was stirred for 20 minutes and ((chloromethoxy)methyl)benzene (0.899 mL, 5.82 mmol) in DMF (3 mL) was then added slowly via syringe. The mixture was stirred a 00C for 30 minutes. Lithium hydride (66.4 mg, 7.94 mmol) was then added in portions and stirred for 10 minutes. Sodium iodide (793 mg, 5.29 mmol) and l-(2-chloroethyl)-l/f-pyrazole (829 mg, 6.35 mmol) were added in portions and then stirred at 00C for 30 minutes. The ice bath was removed. The mixture was stirred at room temperature for 4 hours and then heated to 500C with stirring for 3 days. The reaction mixture was cooled to room temperature. Water (25 mL) and methanol (25 mL) were added and the solvents were evaporated under vacuum at 65°C to give a residue, which was partitioned between IN NaOH (75 mL) and diethyl ether (50 mL). The organic layer was separated and the aqueous layer was washed with diethyl ether (2 x 50 mL). The aqueous layer was then acidified to pH=3 with IN HCl and then extracted with n-BuOH (5 x 100 mL). The organic layers from the n-BuOH extraction were combined and the solvent was evaporated under vacuum to give a residue which was purified by HPLC (40percent ACN in water containing 0.05percent TFA) to give the title compound. MS [M+H] found 371.

The synthetic route of 6153-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FENG, Jun; KEUNG, Walter; LARDY, Matthew; WO2010/129848; (2010); A2;,
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. 2164-65-0, name is 2-Aminopyrimidine-4-carboxylic acid, molecular formula is C5H5N3O2, 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. Product Details of 2164-65-0

To a solution of the HCl salt of 38b, 2-amino-pyrimidine-4-carboxylic acid (30 mg, 0.22 mmol) and EEDQ (54 mg, 0.22 mmol) in DMF was added TEA (56 muL, 0.41 mmol). The reaction mixture was heated to 60 C. More reagent was added and the reaction was stirred at 65 C. until all 38b was consumed. The reaction was concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a Magic/DCM gradient (0% to 20% Magic) which resulted in a slightly impure I-8, which was sequentially washed with DCM and MeOH to afford 6.3 mg of the desired product: MS calcd for C24H17ClN6O2S [M+H]+ 489. Found, 489: 1H NMR (DMSO-d6, 300 MHz): delta 10.49 (broad s, 1H), 8.66 (s, 1H), 8.53 (d, 1H), 7.99-7.79 (m, 5H), 7.48 (m, 4H), 7.16 (d, 1H), 6.95 (bs, 2H), 5.49 (s, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 2164-65-0.

Reference:
Patent; Roche Palo Alto LLC; US2011/70190; (2011); 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. 1074-41-5, name is 6-Amino-2-(methylthio)pyrimidin-4-ol. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Amino-2-(methylthio)pyrimidin-4-ol

General procedure: A mixture of equimolar amounts of 6-amino-2-(methylthio)pyrimidin-4(3H)-one (1) (1 mmol), ethylcyanoacetateor meldrum?s acid (2 or 5) (1 mmol) and aldehyde(3 or 6) (1 mmol) was added to a vial containinga magnetic stirring bar and [DMBSI]HSO4 (0.18 mmol,0.06g) and heated at 80 C in an oil bath. Stirring at 80C was continued until disappearance of the startingmaterials. At this stage, due to the poor solubility in theionic liquid, the product appears as a precipitate. Thereaction mixture was cooled and washed with water toextract the ionic liquid. The solid obtained was recrystallizedfrom ethanol to furnish the desired pure product.The ionic liquid was recovered from the aqueous extractsby evaporation under reduced pressure, and reusedin the next run.

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, 1074-41-5, 6-Amino-2-(methylthio)pyrimidin-4-ol.

Reference:
Article; Nia, Roghayeh Hossein; Mamaghani, Manouchehr; Tabatabaeian, Khalil; Shirini, Farhad; Rassa, Mehdi; Acta Chimica Slovenica; vol. 60; 4; (2013); p. 889 – 895;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 330786-24-8 ,Some common heterocyclic compound, 330786-24-8, molecular formula is C17H13N5O, 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.

Step 1. To a solution of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (300 mg, 1.0 mmole), triphenylphosphine (1.04 g, 3.96 mmole) and tert-butyl (2-hydroxyethyl)carbamate (238 mg, 1.5 mmoles) in THF (25 mL) was added DIAD (0.4 mL, 2mmoles). The reaction was stirred for 5 hrs at room temperature and then water (30 mL) was added and extracted with ethyl acetate. The organic layers were combined, washed with aq. NaHCO3 and brine, then dried (Na2SO4), filtered and concentrated. The resulting tert-butyl (2-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)carbamate was used without further purification.

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. 330786-24-8, 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; BABLER, Martin; GERRITSEN, Mary E.; WO2014/22569; (2014); 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. 157335-97-2, name is 5-Bromo-4,6-dimethylpyrimidine. A new synthetic method of this compound is introduced below., Recommanded Product: 157335-97-2

[1,1 ?-Bis(diphenylphosphino)ferrocene]dichloropalladium(l 1)-dichloromethanecomplex (5 g, 6 mmol) was added to a degassed mixture of 2-(4-methoxy-2-methylphenyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (30 g, 120 mmol), 5-bromo-4,6-dimethylpyrimidine (22.5 g, 120 mmol), and potassium phosphate (76.3 g, 359 mmol) in 1,4-dioxane (300 mL) and water (150 mL). The reaction mixture was heated at reflux for4 hours, whereupon it was filtered and concentrated in vacuo. Purification via silica gel chromatography (Gradient: ethyl acetate in petroleum ether) provided the product as abrown solid. Yield: 25 g, 110 mmol, 92%. LCMS m/z229.3 [M+H]. 1H NMR (300 MHz, ODd3) oe 8.95 (5, 1H), 6.94 (d, J=8.2 Hz, 1H), 6.87-6.89 (m, 1H), 6.84 (dd, J=8.3, 2.5 Hz, 1H), 3.86 (5, 3H), 2.21 (5, 6H), 1.99 (5, 3H).

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, 157335-97-2, 5-Bromo-4,6-dimethylpyrimidine.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; ZHANG, Lei; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/162515; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine, 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, Quality Control of 2,4-Dichloro-5-fluoropyrimidine, blongs to pyrimidines compound. Quality Control of 2,4-Dichloro-5-fluoropyrimidine

(1) Take 100g of 2,4-dichloro-5-fluoropyrimidine and dissolve it in 1000 ml of anhydrous tetrahydrofuran, lower it to a low temperature of 0 C, and add ammonia water dropwise. The speed of ammonia water drop control should be kept at When the temperature exceeds 0 , keep the temperature at 0 for 2 to 3 hours.(2) Naturally rise to room temperature for 1-2 hours, evaporate the solvent, dissolve in ethyl acetate, wash with saturated aqueous sodium bicarbonate solution, wash with saturated brine, dry, filter, and concentrate to obtain 2-chloro-4-amino-5-fluoropyrimidine And 2-amino-4-chloro-5-fluoropyrimidine 88 g;(3) The mixture obtained in step (2) is subjected to column chromatography to obtain 23.44 g of 2-amino-4-chloro-5-fluoropyrimidine, the purity is greater than 98%, and the yield is 26%.

The synthetic route of 2927-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Puruida Pharmaceutical Technology Co., Ltd.; Wang Xiaobo; (4 pag.)CN110343074; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia