Tag: M.W:100-200

Electric Literature of 38275-57-9, 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 38275-57-9, name is 5-Bromopyrimidine-2-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-bromopyrimidine-2-carbonitrile (3.0 g, 16 mmol) in MeOH (20 mL) was added concentrated HCl (19 mL). The reaction mixture was heated at 80 C. for 2 h. Upon cooling to rt, a precipitate formed. Filtration provided the desired product as a white solid (2.5 g, 71%). MS (ESI): mass calcd. for C6H5BrN2O2, 216.0; m/z found, 217.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 9.20 (s, 2H), 3.92 (s, 3H).

According to the analysis of related databases, 38275-57-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Rech, Jason C.; Savall, Brad M.; US2014/275096; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 739364-95-5, 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.739364-95-5, name is 2-Methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid, molecular formula is C8H7N3O2, molecular weight is 177.16, as common compound, the synthetic route is as follows.

DPPA (0.5 mL, 2.31 mmol) and Et3N (1.2 mL, 8.3 mmol) were added at rt to a stirred solution of l-4b (300 mg, 1.69 mmol) in 1,4-dioxane (10 mL). The resulting reaction mixture was stirred at rt for 50 min, then l-3b (500 mg, 2.57 mmol) was added and the reaction mixture was stirred at 100 C for 2 h. When TLC indicated consumption of starting material the reaction mixture was cooled to rt, diluted in water (50 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with brine (50 mL), dried (Na2S04), filtered and concentrated. The crude material was purified by CombiFlash (silica gel) eluted with 8% MeOH in DCM. Fractions containing compound were combined and concentrated and the resulting solid was triturated in MeCN (2 x 5 mL) followed by trituration in EtOH (15 mL). and dried which gave the title compound (100 mg, 15%) as a solid. LCMS (ES+) m/z 369.20 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 739364-95-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MEDIVIR AKTIEBOLAG; ERSMARK, Karolina; KARLSTROeM, Sofia; KLASSON, Bjoern; LUNDGREN, Stina; ROSENQUIST, Asa; SALVADOR ODEN, Lourdes; (155 pag.)WO2018/226150; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 157335-93-8, Adding some certain compound to certain chemical reactions, such as: 157335-93-8, name is 4,6-Dimethylpyrimidine-5-carboxylic acid,molecular formula is C7H8N2O2, 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 157335-93-8.

Step L 4,6-Dimethyl-5-[(4-methyl-4-{(3S)-3-methyl-4-[6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]piperazin-1-yl}piperidin-1-yl)carbonyl]pyrimidine To a solution of (2S)-2-methyl-4-(4-methylpiperidin-4-yl)-1-[6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]piperazine trihydrochloride (100 mg, 0.183 mmol), 4,6-dimethylpyrimidine-5-carboxylic acid (67 mg, 0.22 mmol) in DMF (5 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (97 mg, 0.22 mmol) followed by triethylamine (90 mg, 0.9 mmol). After being stirred at room temperature overnight, a solution of NaHCO3 in water was added. The resulting solution was extracted with EtOAc twice. The combined EtOAc layers were washed with brine, dried over MgSO4 and concentrated. Column chromatography on silica (10-20% MeOH in EtOAc) afforded the title compound (60 mg) as an oil. MS calculated for C28H36F3N5O: (M+H)+ 516; found 516.2.

According to the analysis of related databases, 157335-93-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xue, Chu-Biao; Cao, Ganfeng; Huang, Taisheng; Chen, Lihua; Zhang, Ke; Wang, Anlai; Meloni, David; Anand, Rajan; Glenn, Joseph; Metcalf, Brian W.; US2005/261310; (2005); 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. COA of Formula: C4H3BrN2

INTERMEDIATE 8; Step A; A 3-neck round bottomed flask equipped with an addition funnel and condenser and containing zinc dust (2.45 g, 37.4 mmol) was flame dried. After cooling, and purging the system with nitrogen gas, 6 mL of THF was added, followed by 1,2-dibromoethane (0.298 mL, 3.46 mmol). The mixture was warmed to a vigorous reflux using a heat gun and stirred at reflux for 30 seconds (gas evolution was observed), then cooled to room temperature. The warming and cooling was repeated two more times. Then chlorotrimethylsilane (0.402 mL, 3.17 mmol) was added and the mixture was stirred at room temperature for 20 minutes. N-t-butoxycarbonyl-4-iodo-piperidine (known: Billotte, S. Synlett (1998), 379, 8.97 g, 28.8 mmol) in 15 mL of THF was added over a period of about 1 minutes. The reaction mixture was stirred at 50 C. for 1.5 h, then was cooled to room temperature. Meanwhile, a mixture of tri-2-furylphosphine (267 mg, 1.15 mmol) and Tris(dibenzylideneacetone)-dipalladium(0) chloroform adduct (298 mg, 0.288 mmol) was dissolved in 6 mL of THF under a nitrogen atmosphere, stirred for 15 minutes at room temperature, and added to the organozinc solution. Then a solution of 2-bromopyrimidine (5.50 g, 34.6 mmol) in a mixture of 58 mL of THF and 20 mL of N,N-dimethylacetamide was added. The reaction mixture was warmed to 80 C. and stirred for 3.5 h, then was cooled to room temperature and stirred for 36 h. The reaction mixture was filtered through celite and the filter cake was washed with ethyl acetate. The filtrate was diluted further with ethyl acetate, and washed with saturated NaHCO3 solution. The aqueous layer was back extracted with ethyl acetate, the organic layers were combined and washed twice with water and once with brine. The organic phase was dried over anhydrous MgSO4, filtered, and concentrated. Purification by flash chromatography (silica, stepwise gradient: 25% ethyl acetate/hexane, 40% ethyl acetate/hexane, 60% ethyl acetate/hexane, 80% ethyl acetate/hexane, 100% ethyl acetate) to afford 4.92 g of pure 4-(2-pyrimidyl)-piperidine product (65%). 1H NMR (500 MHz, CDCl3): delta 8.70 (d, J=5.0 Hz, 2H), 7.16 (app t, J=4.5 Hz, 1H), 4.24 (br s, 2H), 3.05 (m, 1H), 2.89 (br m, 2H), 2.01 (br d, J=13 Hz, 2H), 1.84 (dq, J=4.5, 12.5 Hz, 2H), 1.49 (s, 9H).

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:
Patent; Butora, Gabor; Goble, Stephen D.; Pastemak, Alexander; Yang, Lihu; Zhou, Changyou; Moyes, Christopher R.; US2008/81803; (2008); 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

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

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

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 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

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