Day: June 9, 2021

Electric Literature of 5909-24-0 ,Some common heterocyclic compound, 5909-24-0, molecular formula is C8H9ClN2O2S, 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.

After dissolving 50.0 g of 4-chloro-5-ethoxycarbonyl-2-methylthiopyrimidine and 59.9 ml of triethylamine into 430 ml of ethyl acetate, respectively, the mixture was cooled to 0 C, 44.7g of 3-chloro-4-methoxybenzylamine was added in portions, the reaction was carried out at 0-5 C for 30min and the reaction was continued at 20-30 C for 0.5-1h. The reaction was concentrated under reduced pressure, and then added ethyl acetate and citric acid solution 400ml each wash 2 times, the organic phase was washed with water and saturated brine each time, dried, filtered and concentrated under reduced pressure to give the crude 73.0g. Finally, with anhydrous ethanol at 55 ~ 60 C dissolved crude, stirring crystallization 12-18h, filtered and dried to give the product 42.3g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5909-24-0, its application will become more common.

Reference:
Patent; Guangzhou Langsheng Pharmaceutical Co., Ltd.; Chen Yuhua; Lu Pingping; Mo Enqing; Zuo Lian; Lu Zhijun; Peng Guizi; Yuan Yongling; (14 pag.)CN104059025; (2017); B;,
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. 372118-67-7, name is Pyrimidin-2-ylmethanamine hydrochloride, the common compound, a new synthetic route is introduced below. category: pyrimidines

To a solution of 2-((6,8-dichloro-3-(methoxycarbonyl)naphthalen-1 – yl)(methyl)annino)acetic acid (60 mg, 0.18 mmol) in DMF (1 ml_) is added CDI (40 mg, 0.25 mmol), and the mixture is heated at 50 C for 30 min. Then pyrimidin-2- ylmethanamine hydrochloride (36 mg, 0.25 mmol) and DIPEA (34 mg, 0.26 mmol) are added, and the reaction mixture is stirred at 50 C for 3 days (LC-MS control). The mixture is allowed to cool to rt, diluted with water (5 mL) and brine (6 mL), and extracted with EtOAc (4x). The organic extracts are combined, dried over Na2SO4, filtered and evaporated. The residue is purified by flash chromatography on silica (eluent – EtOAc:hexane or DCM:MeOH) to give the title compound in 72% yield as a yellow oil.

The synthetic route of 372118-67-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; ABEL, Ulrich; HANSEN, Angela; WOLTER, Falko Ernst; KRUEGER, Bjoern; KAUSS, Valerjans; ROZHKOVS, Jevgenijs; PISKUNOVA, Irena; ZVAGULIS, Artis; TRIFANOVA, Dina; GRUNSTEINE, Ginta; TURE, Anastasija; WO2013/30358; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 932-52-5, 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 932-52-5 as follows.

8-(2,6-Difluorophenyl)-4-(4-fluoro-2-methlphenyl)-2-(N-aminouracil-5-yl)-8H-pyrido[2,3-d]pyrimidin-7-one The title compound of Example 48 [8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one] (100 mg, 0.000225 mol) and 5-aminouracil (70 mg, 0.00055 mol) were taken up in dry DMSO (1.5 ML) and, with stirring under Ar, warmed to 65 for 6.5 h.Reaction was cooled to 23, then diluted with EtOAc; solution was washed with H2O; the aq phase was extracted with EtOAc; combined organic layers were dried (Na2SO4) then evaporated to an amber glass.This glass was crystallized from a small amount of MeOH, which crystals when dried afforded 15 mg (14%) of the title compound as a light yellow crystalline solid. (m.p.>300) LC MS (m/e)=493(MH+). Rt=1.82 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,932-52-5, its application will become more common.

Reference:
Patent; Adams, Jerry L.; Boehm, Jeffrey C.; Hall, Ralph; Jin, Qi; Kasparec, Jiri; Silva, Domingos J.; Taggart, John J.; US2004/116697; (2004); 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. 7461-50-9, name is 2-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, 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. COA of Formula: C4H4ClN3

In a reaction apparatus with a reflux condenser, 2,3-dimethyl-6-chloro-2H-carbazole 18gAnd 14.5 g of 2-chloro-4-amino-pyrimidine were added to 220 mL of N,N-dimethylformamide.In an ice salt bath at 0 C under nitrogen protection,50 mL of a tetrahydrofuran solution containing 12% of sodium hydride in a content of 60% was slowly added dropwise.After the addition was completed, the temperature was raised to room temperature, and the reaction was continued for 5 hours.Then use the existing strong alkaline environment of the reaction system,100 mL of tetrahydrofuran solution in which 14 g of methyl iodide was dissolved was added dropwise.The reaction was continued for 6 h at room temperature, and new substances appeared in the reaction system monitored by TLC.And the content of the new substance in the reaction system is determined by HPLC to occupy 90% to 95%,The reaction system was cooled to 10 C, and then dilute hydrochloric acid was slowly added dropwise.The pH of the reaction solution was adjusted to be neutral, and then tetrahydrofuran was removed by evaporation under vacuum.The reaction solution was allowed to stand for a while, and then 70 mL of a saturated ammonium chloride solution was added to the reaction solution.Then, 250 mL of chloroform was added to the reaction solution.After stirring for 10 min, the organic phase was separated and the organic phase was concentrated.The concentrate is recrystallized from acetone and cyclohexane to giveN-(2-chloropyrimidin-4-yl)-N-methyl-2,3-dimethyl-2H-indazole-6-amine 20.7 g;

With the rapid development of chemical substances, we look forward to future research findings about 7461-50-9.

Reference:
Patent; Jinan Ai Si Pharmaceutical Technology Co., Ltd.; Peng Lizeng; Mao Longfei; Liu Xiaofei; Yao Xiaojun; Liu Huanxiang; Bai Qifeng; Liang Lixian; (17 pag.)CN110028495; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 271-70-5, 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.271-70-5, name is 7H-Pyrrolo[2,3-d]pyrimidine, molecular formula is C6H5N3, molecular weight is 119.124, as common compound, the synthetic route is as follows.

To the 7H-pyrrolo[2,3-djpyrimidine (6 g, 50.4 mmol) andhexamethylaminetetramine (10.59 g, 76 mmol) were added acetic acid (20.00 mL) andwater (40 mL) under nitrogen. The reaction mixture was heated to reflux and stirred for 8hs. The reaction mixture was cooled to r.t then filtered the solid. The solid was washed with ether for 3 times. The solid was dried to afford 7H-pyrrolo[2,3-djpyrimidine-5-carbaldehyde 5.6 g(76%) as desired product. ESI-MS(+): MS m/z 148.1.?HNMR (METHANOL-d4) & 10.00 (s, 1H), 9.43 (s, 1H), 8.91 (s, 1H), 8.40 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 271-70-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MILLER, Michael Matthew; ALLEN, Martin Patrick; LI, Ling; BOWSHER, Michael S.; GILLIS, Eric P.; MULL, Eric; ZHAO, Qian; SUN, Li-Qiang; LANGLEY, David R.; SCOLA, Paul Michael; (214 pag.)WO2017/176608; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 137281-39-1, 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. 137281-39-1, name is 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid. A new synthetic method of this compound is introduced below.

4. 4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (60 g 0.2 mol) Add to a 500ml four-neck bottle,Add 200ml of DMF and 40.4g of triethylamine to warm up to 30C and stir to dissolve.Trityl chloride (0.3 mol) was added dropwise, and the reaction was kept at 35 C for 1 hour.Evaporate DMF under reduced pressure,Add 200ml of pure water and stir.Adjust the pH to 5-6 with dilute hydrochloric acid, stir the crystallization,Cool down to 0-5C suction filtration,Drying the product 4-[2-(2-tritylamino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (molar yield 96.3%, purity 99.2%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,137281-39-1, 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; Lunan Pharmaceutical Group Co., Ltd.; Zang Chao; Xia Mingjun; (11 pag.)CN110305136; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3993-78-0, 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. 3993-78-0, name is 2-Amino-4-chloropyrimidine. A new synthetic method of this compound is introduced below.

To a solution of 2-fluoro-5- (tetramethyl-l,3,2-dioxaborolan-2-yl)benzonitrile (1.71 g, 6.92 mmol) in dioxane (40 mL) was added 4-chloropyrimidin-2-amine (950 mg, 7.33 mmol), sodium carbonate solution (1.4 M in water, 10 mL, 14.00 mmol) and Pd(PCyg)2Ci2 (1.08 g, 1.47 mmol) at room temperature. The resulting mixture was stirred for 3 h at 100 C. When the reaction was done, the reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in hexane (0 % to 100 % gradient) to yield 5-(2-aminopyrimidin-4-yl)-2- fluorobenzonitrile as an yellow solid (990 mg, 66 %). MS: m/z = 215.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3993-78-0, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; KARRA, Srinivasa R.; XIAO, YuFang; SHERER, Brian A.; (380 pag.)WO2019/79373; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1780-26-3, 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. 1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine. A new synthetic method of this compound is introduced below.

5 mmol of N,N-dimethylglycine, 2 mmol of CuI, 20 mmol of 4,6-dichloro-2-methylpyrimidine were dissolved in 100 mL of N,N-dimethylformamide (DMF), and stirred.22 mmol of N-hydroxyethylpiperazine and 40 mmol of K3PO4 were added, and the mixture was stirred at room temperature for 40 min, and 22 mmol of 2-amino-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide was added with stirring. After reacting with N2 at 120 C for 6 h, 50 mL of aqueous ammonia was added to dissolve the copper salt, and extracted with 50 mL of 3 ethyl acetate. The ethyl acetate phase was combined and washed with saturated brine.The organic layer was dried over anhydrous Na 2 SO 4 .Get a rough product. The crude product was added to 100 mL of an 80% aqueous solution of ethanol, stirred, and 2 g of activated carbon was added, refluxed for 30 min, filtered while hot, and the filtrate was recrystallized overnight, filtered, and the filter cake was washed with ice-cold 80% aqueous ethanol, and dried to give a white solid 8.64. g, yield 88.41%, purity 99.92%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1780-26-3, 2-Methyl-4,6-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Shandong Luoxin Pharmaceutical Group Co., Ltd.; Shandong Luoxin Pharmaceutical Group Hengxin Pharmaceutical Co., Ltd.; Shandong Yuxin Pharmaceutical Co., Ltd.; Liu Zhenteng; Zhu Xuhui; Xie Youcui; (13 pag.)CN109796448; (2019); A;,
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. 672-41-3, name is 6-(Trifluoromethyl)pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. name: 6-(Trifluoromethyl)pyrimidin-4-amine

A sample of 6-(trifluoromethyl)pyrimidin-4-amine (73.7 mg, 0.45 mmol, CAS number: [672-41-3]) and 2-bromo-1-(5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)ethanone (150 mg, 0.45 mmol) were dissolved in acetonitrile (3 mL) and the resulting mixture stirred for 1 h at 150C in a Microwave system. LCMS showed the formation of product after this time. The reaction mixture concentrated in vacuo, and the residue obtained dissolved in dichloromethane and washed with saturated aqueous NaHC03. The aqueous layer back-extracted (2 times) with dichloromethane and the combined organic layers washed with NH4OH 1 N, brine, dried over Na2S04 and concentrated in vacuo.. The crude product was purified by combi flash chromatography with a column of 12 g and a gradient dichloromethane +0-20% ethyl acetate. The product so obtained was triturated with ethyl acetate,to give the title compound as white solid LCMS (method 1 ); Rt= 0.98 min, [M+H] 397 H NMR (400 MHz, CHLOROFORM-c/) delta ppm 0.87 – 0.94 (m, 2 H) 1.18 – 1.24 (m, 2 H) 1.34 (t, J=7.34 Hz, 3 H) 2.03 – 2.12 (m, 1 H) 3.84 (q, J=7.34 Hz, 2 H) 7.95 (s, 1 H) 8.10 (d, J=2.20 Hz, 1 H) 8.31 (s, 1 H) 8.68 (d, J=2.20 Hz, 1 H) 9.15 (s, 1 H)

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, 672-41-3, 6-(Trifluoromethyl)pyrimidin-4-amine.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; EDMUNDS, Andrew; JEANGUENAT, Andre; JUNG, Pierre Joseph Marcel; MUEHLEBACH, Michel; (150 pag.)WO2016/71214; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 14048-15-8 ,Some common heterocyclic compound, 14048-15-8, molecular formula is C6H9N3O2, 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.

2,6-Di-tert-butyl-4-[(2,4-dimethoxypyrimidin-5-yl)amino]phenol was synthesized using the same method as described for 4-[(5-bromo-3-methoxypyrazin-2-yl)amino]-2,6-di-tert- butylphenol in Example 2. 387 mg (2.9 mmol) of A1C13, 0.55 ml of pyridine, 20 ml of 1,2- dichloroethane, 255 mg (1.16 mmol) of 2,6-di-tert-butyl-l,4-benzoquinone, and 180 mg (1.16 mmol) of 2,4-dimethoxypyrimidin-5-amine was used. Reaction time in the imine formation stage was 17 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. 14048-15-8, 2,4-Dimethoxypyrimidin-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDEIA THERAPEUTICS LTD; GOLDSTEINS, Gundars; KOISTINAHO, Jari; KOISTINAHO, Milla; RATILAINEN, Jari; PYSTYNEN, Jarmo; WO2014/68171; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia