Day: August 19, 2021

Related Products of 6299-25-8 ,Some common heterocyclic compound, 6299-25-8, molecular formula is C5H4Cl2N2S, 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 mixture of 4,6-dichloro-2-(methylsulfanyl)pyrimidine (1-180) (20.0 g, 102.53 mmol) and oxone (189.0 g, 308 mmol) in THF (450 mL) and H20 (150 mL) was stirred at room temperature for 16 hr. TLC (Petroluem ether : EtOAc = 1 : 1) showed the starting material had been consumed. The reaction mixture was filtered and washed with THF (100 mL). The combined filtrate was concentrated, dissolved in EtOAc (500 mL) and washed with H20 (2 x 300 mL) and brine (300 mL). The organic layer was dried over Na2S04 and concentrated. The residue was purified by silica gel chromatography (petroleum ether : EtOAc = 10 : 1 to pure EtOAc) to give 4,6-dichloro- 2-(methylsulfonyl)pyrimidine (1-174) (20 g, 86 %) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6299-25-8, its application will become more common.

Reference:
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); 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. 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. category: pyrimidines

To a solution of 4-chloro-7H-pyrrolo[2,3-Patent; MERCK SHARP & DOHME CORP.; AHEARN, Sean, P.; CHRISTOPHER, Matthew; JUNG, Joon; PU, Qinglin; RIVKIN, Alexey; SCOTT, Mark, E.; WITTER, David, J.; WOO, Hyun Chong; CASH, Brandon; DINSMORE, Christopher; GUERIN, David; WO2013/85802; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 14394-70-8 ,Some common heterocyclic compound, 14394-70-8, molecular formula is C5H6ClN3, 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.

[0460] A mixture of 3-bromopyridine (379 mg, 2.4 mmol), 4-amino-2-chloro-5- methylpyrimidine (287 mg, 2.0 mmol), Pd2(dba)3 (18 mg, 0.02 mmol), xantphos (23 mg, 0.04 mmol) and cesium carbonate (975 mg, 3.0 mmol) in dioxane ( 15 mL) was heated under refluxed for 1 h under argon. The solvent was removed and the residue on purification by HPLC gave an intermediate, 2-cliloro-5-methyl-iV-(rhoyridin-3-yl)pyrimidin-4-amine as yellow solid (252 mg, 57%). For second Buckwald, a mixture of 2-chloro-5-methyl-iV-(pyridin-3- yl)rhoyrimidin-4-amine (80 mg5 0.36 mmol), 4-(2-(pyrrolidin-l-yl)ethoxy)benzenamine (74 mg, 0.34 mmol), Pd2(dba)3 (3.2 mg, 0.003 mmol), xantphos (4.2 mg, 0.007 mmol) and cesium carbonate (234 mg, 0.72 mmol) in dioxane ( 5 mL) was heated under refluxed for 1 h under argon. The crude reaction mixture on purification using HPLC gave the title compound as light brown solid (28 mg, 20%).[0461] 1H NMR (500 MHz, DMSOd6): 8 1.85-1.95 (m, 2H), 2.0-2.09 (m, 2H)3 2.18 (s, 3H), 3.09-3.18 (m, 2H), 3.55-3.65 (m, 4H), 4.27 (dd, J= 5.2, 4.7 Hz, 2H), 6.94 (d, J= 8.9 Hz, 2H), 7.35 (d, J= 8.9 Hz, 2H), 7.50 (dd, J= 8.2, 4.8 Hz, lH),7.92-7.96 (m, IH), 8.08-8.15 (m, IH), 8.45 (dd, J= 4.8, 1.4, IH), 8.84, 9.75, 9.85, 10.24 (4 br s, IH each). MS (ES+): m/z 329 (M+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. 14394-70-8, 2-Chloro-5-methylpyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); 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. 16357-69-0, name is 4-Aminopyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H4N4

Compound 1e (1 mmol, 120 mg), [HDBN+][TFE-] (6 mmol, 1.35 g)was added to a 10 ml round-bottomed flask.in CO2 Under the environment, heating to 90 C for 48 hours, stop the reaction, until the temperature cools to room temperature, add saturated NH4Aqueous Cl solution to adjust the pH to neutral, respectively 20ml CH2Cl2Extract three times and collect CH2Cl2The solution was dried over anhydrous sodium sulfate, filtered, and the solution was evaporated under reduced pressure. The solid was isolated by silica gel column chromatography (eluent CH2Cl2_CH3OH=15:1) 131 mg of white solid compound 2e was obtained with a yield of 80%.

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, 16357-69-0, 4-Aminopyrimidine-5-carbonitrile.

Reference:
Patent; Guizhou Medical University; Li Chun; Zhang Lin; Yang Yuanyong; (11 pag.)CN107698587; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 330786-24-8, 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 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

The 3- (4-phenoxyphenyl) -1H-pyrazolo [3,4-d]pyrimidin-4-amine(compound 2a)(2.12g,7mmol), 3-hydroxypiperidine-1- tert-Butyl formate(1.55g,7.7mmol), Triphenylphosphine(2.75g,10.5mmol)and Azobisisobutyronitrile (2.12g,10.5mmol) dissolved in THF (250ml), keep thereaction at room temperature for 12h(TLC thin layer chromatography monitoringreaction is complete or not). After the completion of the reaction , solventwas recovered under reduced pressure. into the remaining reaction mixture added100 ethyl acetate, organic layer was extracted three times with Saturatedsodium carbonate solution 100ml*3, organic phases were combined, washed oncewith saturated sodium chloride and dried over anhydrous sodium sulfate. The solvent was recovered under reducedpressure to give 1.12 g of a brown solid in 33% yield.

According to the analysis of related databases, 330786-24-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HANGZHOU HERTZ PHARMACEUTICAL CO LTD; ZHOU, XINGLU; HAN, LING; GE, ZHEN; LIU, XINGGUO; LUO, WENHUA; LIU, WENHUA; (27 pag.)CN104844609; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 583878-42-6, 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.583878-42-6, name is Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate, molecular formula is C9H11ClN2O2S, molecular weight is 246.71, as common compound, the synthetic route is as follows.

Intermediate 1 1Ethyl 4-({3-r3-({r(1 , 1-dimethylethyl)oxylcarbonyl}amino)propyllphenyl}amino)-6-methyl-2-(methylthio)-5-pyrimidinecarboxylateTo a solution of 1 ,1-dimethylethyl [3-(3-aminophenyl)propyl]carbamate (390 mg, 1.558 mmol) in DMF (5 ml.) were added ethyl 4-chloro-6-methyl-2-(methylthio)-5- pyrimidinecarboxylate (307 mg, 1.246 mmol) and DIEA (0.298 ml_, 1.714 mmol), and the reaction mixture was stirred at 75 0C overnight. The reaction was then concentrated and the residue was purified using column chromatography (silica gel, 0% to 50% EtOAc gradient in hexane) to afford the product (210 mg, 29% yield). MS: M(C23H32N4O4S) = 460.59, (M+H)+ = 461.6 1 H NMR (400 MHz, CD3OD) delta ppm 1.44 – 1.47 (m, 12 H), 1.77 – 1.85 (m, 3 H), 2.52 (s, 3 H), 2.62 (s, 3 H), 2.65 (d, J = 8.6 Hz, 2 H), 3.09 (t, J = 7.0 Hz, 2 H), 4.45 (q, J = 7.2 Hz, 2 H), 4.64 (br. s., 1 H), 7.01 (d, J = 7.6 Hz, 1 H), 7.28 (t, J = 7.8 Hz, 1 H), 7.42 (d, J = 1.3 Hz, 1 H), 7.55 – 7.58 (m, 1 H).

The chemical industry reduces the impact on the environment during synthesis 583878-42-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; ATKINSON, Francis, Louis; AXTEN, Jeffrey, Michael; CICHY-KNIGHT, Maria; MOORE, Michael, Lee; PATEI, Vipulkumar, Kantibhai; TIAN, Xinrong; WELLAWAY, Christopher, Roland; DUNN, Allison, K.; WO2010/19637; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 13223-25-1

Example 5 Synthesis of 3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde diethylacetal (Compound No. 3) Step (d)] Sodium hydride (7.0 g) was added under stirring to 300 ml of dimethylimidazolidinone, followed by the gradual addition of 37.5 g of 3-hydroxy-2-pyridinecarboxaldehyde diethylacetal at room temperature. Heat was evolved with bubbling so that the temperature of the mixture arose to 55 C. After the mixture was heated for 1 hour at 90-95 C., 31.6 g of 2-chloro-4,6-dimethoxypyrimidine were added. The reaction mixture was heated at 100-120 C. for 8 hours so that the reaction was brought to completion. The reaction mixture was cooled to room temperature, added with 500 ml of water, and then extracted three times with 700 ml portions of ethyl acetate. The organic layers were combined, washed with water and then dried over anhydrous sodium sulfate. The solvent was then distilled out, whereby 87.4 g of an oily residue were obtained. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=1:1) so that 54.6 g of 3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde diethylacetate were obtained (yield: 90%).

With the rapid development of chemical substances, we look forward to future research findings about 13223-25-1.

Reference:
Patent; Mitsui Toatsu Chemicals Incorporated; US5129937; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 444731-75-3, 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. 444731-75-3, name is N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine, molecular formula is C14H14ClN5, 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.

To a solution of Intermediate Example 4 (200 mg, 0.695 mmol) and 5-amino-2- methylbenzenesulfonamide (129.4 mg, 0.695 mmol) in isopropanol (6 ml) was added 4 drops of cone. HCI. The mixture was heated to reflux overnight. The mixture was cooled to rt and diluted with ether (6 ml). Precipitate was collected via filtration and washed with ether. The hydrochloride salt of 5-({4-[(2,3-dimethyl-2H-indazol-6- yl)(methyl)amino]-pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide was isolated as an off-white solid. 1H NMR (400 MHz, d6DMSO+NaHCO3) delta 9.50 (br s, 1 H), 8.55 (br s, 1 H), 7.81 (d, J = 6.2 Hz, 1 H), 7.75 (d, J = 8.7 Hz, 1 H), 7.69 (m, 1 H), 7.43 (s, 1 H), 7.23 (s, 2H), 7.15 (d, J = 8.4 Hz, 1 H), 6.86 (m, 1 H), 5.74 (d, J = 6.1 Hz, 1 H), 4.04 (s, 3H), 3.48 (s, 3H), 2.61 (s, 3H), 2.48 (s, 3H). MS (ES+, m/z) 438 (M+H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 444731-75-3, N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/20564; (2006); 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.205672-25-9, name is 4-Amino-5-bromo-2-chloropyrimidine, molecular formula is C4H3BrClN3, molecular weight is 208.44, as common compound, the synthetic route is as follows.Computed Properties of C4H3BrClN3

Synthesis of 2-Chloro-5- (2-ethoxyvinyl)-pyrimidin-4-ylamine (2):; A 500 mL round bottomed flask is charged with 5-bromo-2-chloropyrimidin-4-ylamine (1) (lOg, 48 mmol), tetrakis (triphenylphosphine) palladium (0) (2.8g, 2.5 mmol), and toluene (200 mL). Tributyl- (2-ethoxyvinyl)-stannane (22g, 60 mmol) is added and the reaction heated to 110C with stirring for approximately 15 hours. After cooling to room temperature, the solution is diluted with 100 mL ethyl acetate and washed with water and brine. The organic extract is dried over Na2S04, filtered, and concentrated under reduced pressure. Purification by column chromatography (Si02, Hexane: Ethyl acetate/5: 1) provides 2 (4.4 g, 46%) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,205672-25-9, 4-Amino-5-bromo-2-chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; IRM LLC; WO2005/80393; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 25193-95-7, 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. 25193-95-7, name is 5-(Hydroxymethyl)pyrimidine, molecular formula is C5H6N2O, 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.

Into 2 g of N,N-dimethylformamide were dissolved 219 mg of 5-chloro-3-benzylthio-1,2,4-thiadiazole and 200 mg of 5-pyrimidylmethyl alcohol, 44 mg of sodium hydride (60% in oil) was added thereto under ice-cooling, and the reaction mixture was stirred for 30 minutes. After stirring for 5 hours at room temperature, the reaction mixture was added to saturated sodium chloride aqueous solution, and extracted with t-butyl methyl ether. The organic layer was concentrated, and the residue obtained was subjected to silica gel column chromatography to give 130 mg of 5-(5-pyrimidylmethyloxy)-3-benzylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (38)). [] 1H-NMR: 9.25 (s, 1H), 8.86 (s, 2H), 7.43-7.24 (m, 5H), 5.53 (s, 2H), 4.41 (s, 2H)

According to the analysis of related databases, 25193-95-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP1475374; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia