Day: March 25, 2022

Electric Literature of 17180-94-8, 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 17180-94-8, name is 5-Chloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis 193-(5-Chloro-pyrimidin-4-yl)-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl estern-Butyl lithium (2.5 , 1.2 mL, 3.00 mmol) was added dropwise to a solution of diisopropylamine (0.406 mL, 3.0 mmol) in THF (5 mL) at 0C under nitrogen and stirred for 30 minutes. The mixture was then added to a solution of 3-oxo-8-aza- bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.675 g, 3.0 mmol) and 5- chloropyrimidine (0.343 g, 3.0 mmol) in THF (1.5 mL) and stirred at 0C for 1 hour. Water and ethyl acetate were added, the organics separated, dried over sodium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 20-30% ethyl acetate/cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.14 g). LCMS m/z 340.3 [M+H]+. R.T. = 3.70 min (Analytical Method 3).

According to the analysis of related databases, 17180-94-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF EDINBURGH; WEBSTER, Scott, Peter; SECKL, Jonathan, Robert; WALKER, Brian, Robert; WARD, Peter; PALLIN, Thomas, David; DYKE, Hazel, Joan; PERRIOR, Trevor, Robert; WO2011/135276; (2011); 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 499195-60-7, name is Ethyl 4-(2-chloropyrimidin-4-yl)benzoate. This compound has unique chemical properties. The synthetic route is as follows. Safety of Ethyl 4-(2-chloropyrimidin-4-yl)benzoate

Step I : Preparation of ethyl 4-(2-((4-(4-(6-oxa-3-azabicyclo[3.1.1]heptan-3- yl)piperidin- 1 -yl)phenyl)amino)pyrimidin-4-yl)benzoate. Placed ethyl 4-(2-chloropyrimidin-4-yl)benzoate [4.37 g, 16.64 mmol] in rb flask followed by DMA [60 mL]. To this, 4-(4-(6-oxa-3-azabicyclo[3.1.1]heptan-3- yl)piperidin-l-yl)aniline (Amine 17) [3.5 g, 12.80 mmol], cesium carbonate [6.26 g, 19.20 mmol], BINAP [1.19 g, 1.92 mmol] and bis triphenyl phosphie Pd (Il)dichloride [1.34 g, 1.92 mmol] was added at 25C under N2 atm. The mixture was heated to 90C for 16 h. After completion of reaction mixture was quanched in water, compound was extracted with ethyl acetate (50 mL X 4), Combined the organic layers and washed with water and brine soln. The organic layer was dried over Na2S04, filtered and concentrated under reduced pressure to afford desired product as light yellow solid. Title compound was characterised by spectral analysis. ESI-MS : 500.30 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 499195-60-7.

Reference:
Patent; CADILA HEALTHCARE LIMITED; DESAI, Ranjit, C.; DESAI, Jigar; PATEL, Pankaj; WO2015/19365; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 923282-39-7 ,Some common heterocyclic compound, 923282-39-7, molecular formula is C6H5ClN4, 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.

Compound 13.1 (100 mg, 0.59 mmol, 1.00 eq.) was dissolved in 5 mL of CH3CN. Then Na2C03 (190 mg, 1.79 mmol, 3.00 eq.) and compound 1.2 (229 mg, 0.89 mmol, 1.50 eq.) were added. The reaction was stirred overnight at 80 C in an oil bath. The resulting mixture was concentrated in vacuo, diluted with 10 mL of H20 and extracted with 3×20 mL of EtOAc. Organic layers were combined and concentrated in vacuo. The crude product was purified by preparative HPLC to furnish 150 mg (80%) of I-13 as a white solid. LC-MS (ESI, m/z): [M+H]+ = 317; 1H- NMR (400 MHz, MeOD): delta 8.23 (s, 1H), 7.88 (s, 1H), 4.86 (s, 1H), 4.20-4.35 (m, 8H), 3.73-3.75 (d, 3H), 3.33 (s, 1H), 2.64-2.66 (d, 3H), 2.32-2.38 (m, 4H), 2.21-2.24 (s, 2H), 1.95-2.11 (m, 4H), 1.44-1.61 (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,923282-39-7, its application will become more common.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; BOYCE, Sarah; (135 pag.)WO2017/4133; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3438-55-9, 5-Bromo-4-chloro-6-methylpyrimidine, 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, 3438-55-9, blongs to pyrimidines compound. SDS of cas: 3438-55-9

95-Bromo-6-methylpyrimidine-4-carbonitrile was prepared from 5-bromo-4-chloro-6-methylpyrimidine via reaction with potassium cyanide and l,4,7,l0,13,16-hexaoxacyclooctadecane. 4-Bromo-3-fluorophenol was converted to [3-fluoro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phe- noxy][tri(propan-2-yl)]silane using the conditions outlined in footnote 5. These two reagents were subjected to Suzuki reaction and desilylation as described in footnote 5, affording 5-(2-fluoro-4-hydroxyphenyl)-6-methylpyrimidine-4-carbonitrile.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3438-55-9, its application will become more common.

Reference:
Patent; PFIZER INC; DAVOREN, JENNIFER ELIZABETH; DOUNAY, AMY BETH; EFREMOV, IVAN VIKTOROVICH; GRAY, DAVID LAWRENCE FIRMAN; MENTE, SCOT RICHARD; O’NEIL, STEVEN VICTOR; ROGERS, BRUCE NELSEN; SUBRAMANYAM, CHAKRAPANI; ZHANG, LEI; US2014/128374; (2014); 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. 43088-67-1, name is 4-Chloro-5-methylthieno[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 43088-67-1

Production Example 190. 4-(2-indanylamino)-5-methylthieno[2,3-d]pyrimidine 4-chloro-5-methylthieno[2,3-d]pyrimidine (92 mg, 0.50 mmol) (see J. Pharm. Soc. JAPAN, 109, 464 (1989)) and 2-aminoindan (330 mg, 2.5 mmol) in dry ethanol (1 ml) were heated to reflux under an argon atmosphere for 40 minutes. The solvent was distilled off under reduced pressure and the residue obtained was purified by silica gel chromatography (hexane: ethyl acetate = 5: 1) toobtain the title compound (140 mg, 0.50 mmol) having the following physical properties: 1H NMR (400 MHz, CDCl3): delta 2.47 (3H, s), 2.94 (2H, m), 3.50 (2H, m), 5.11 (1H, m), 5.65 (1H, br.), 6.80 (1H, s), 7.19-7.27 (4H, m), 8.47 (1H, s). MS (FAB): m/z 282 (M+H)+.

The synthetic route of 43088-67-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNTORY LIMITED; EP1132093; (2001); 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.1126-44-9, name is 2-Methylsulfanylpyrimidine-4-carboxylic acid, molecular formula is C6H6N2O2S, molecular weight is 170.189, as common compound, the synthetic route is as follows.Safety of 2-Methylsulfanylpyrimidine-4-carboxylic acid

The starting material 2-methylsulfanyl-pyrimidine-4-carboxylic acid methoxy-methyl-amide can be prepared as follows. Preparation of 2-methylsulfanyl-pyrimidine-4-carboxylic acid methoxy-methyl-amide: To a slurry of 2-methylsulfanyl-pyrimidine-4-carboxylic acid (10.0 g, 59.2 mmol) in CH3CN (300 mL) is added in sequence: I-hydroxybenzotriazole hydrate (9.59 g, 71.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (13.6 g, 71.0 mmol), N,O-dimethylhydroxylamine hydrochloride (8.66 g, 88.8 mmol), and triethylamine (Et3N) (24.9 mL, 178 mmol). The resulting slurry is stirred overnight at ambient temperature. After 16 hours, the reaction mixture is poured into a saturated aqueous solution of sodium bicarbonate (300 mL) and the layers separated. The aqueous layer is extracted with ethyl acetate (3×250 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo and the resulting residue is purified over silica (100% EtOAc) to afford 10.1 g (89% yield) of the desired product as a yellow oil. 1H NMR (300 MHz, CDCl3) delta 8.65 (d, J=4.9 Hz, 1H), 7.15 (br s, 1H), 3.77 (br s, 3H), 3.38 (br s, 3H), 2.61 (s, 3H); MS (ESI) m/z 214 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1126-44-9, 2-Methylsulfanylpyrimidine-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; The Procter & Gamble Company; US2005/113392; (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. 313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 313339-35-4

3.0 g (12.55 mmol, 1.0 eq) of 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid was dissolved in 40 mL of anhydrous toluene, to which 15 mL of thionyl chloride (SOCl2) was added, followed by stirring at 115 C. for 12 hours. The reaction solvent was concentrated under reduced pressure and dried to give acid chloride. Then, 1.6 g of 5-chloro-7-(methylthio)pyrimido[4,5-d]pyrimidine-4(1H)-one was prepared as a white solid according to the same manner as described in step 2 of Example 66 (2 step yield: 56%). 1H NMR (300 MHz, DMSO-d6) delta 2.56-2.58 (d, J=6.0, 3H), 8.42-8.44 (d, J=6.0, 1H), 12.88 (br 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, 313339-35-4, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Lee, Ge Hyeong; Lim, Hee-Jong; Cho, Heeyeong; Park, Woo Kyu; Kim, Seong Hwan; Choi, Jung Hwan; (148 pag.)US2018/105527; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 175277-33-5, Adding some certain compound to certain chemical reactions, such as: 175277-33-5, name is 4-(Dimethoxymethyl)-2-methylpyrimidine,molecular formula is C8H12N2O2, 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 175277-33-5.

3N HClaq (30 mL, 90.00 mmol) was added to 4-(dimethoxymethyl)-2-methylpyrimidine (3 g, 17.84 mmol) at room teperature. The resulting solution was stirred at 50 C for 4 hours. The solvent was removed under reduced pressure to afford 2-methylpyrimidine-4- carbaldehyde (2.50 g, 88 %) as a red oil. ?H NMR (DMSO, 24 C, 400Hz) 2.81 (3H, s), 7.71(1H, d), 9.02 (1H, d), 9.93 (1H, s). mlz (ES+), [M+H]+ = 123.

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. 175277-33-5, 4-(Dimethoxymethyl)-2-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 199678-12-1, Adding some certain compound to certain chemical reactions, such as: 199678-12-1, name is 4-Pyrimidin-2-yl-benzoic acid,molecular formula is C11H8N2O2, 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 199678-12-1.

Example 138 N-(4-{trans-2-[(cyclopropylmethyl)amino]cyclopropyl}phenyl)-4-(pyrimidin-2-yl)benzamide hydrochloride By a method similar to Example 80, the title compound (34.3 mg) was obtained from tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate (87.7 mg) and 4-(pyrimidin-2-yl)benzoic acid (69.7 mg). MS (API+): [M+H]+ 385.1. 1H NMR (300 MHz, DMSO-d6) delta 0.30-0.42 (2H, m), 0.53-0.66 (2H, m), 0.98-1.12 (1H, m), 1.24-1.35 (1H, m), 1.43-1.55 (1H, m), 2.39-2.46 (1H, m), 2.86-3.07 (3H, m), 7.19 (2H, d, J = 8.6 Hz), 7.53 (1H, t, J = 4.9 Hz), 7.75 (2H, d, J = 8.7 Hz), 8.11 (2H, d, J = 8.6 Hz), 8.53 (2H, d, J = 8.6 Hz), 8.97 (2H, d, J = 4.9 Hz), 9.06 (2H, brs), 10.37 (1H, s).

According to the analysis of related databases, 199678-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; TOMITA, Naoki; KAJII, Shigeo; CARY, Douglas Robert; TOMITA, Daisuke; IMAMURA, Shinichi; TSUCHIDA, Ken; MATSUDA, Satoru; HARA, Ryujiro; EP2743256; (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. 32998-03-1, name is 2,6-Dichloro-N-methylpyrimidin-4-amine. A new synthetic method of this compound is introduced below., COA of Formula: C5H5Cl2N3

EXAMPLE 3 4-Methylamino-2,6-di-1-pyrrolidinopyrimidine (V) Pyrrolidine (IV, 25 ml) is added (exothermic) to 2,6-dichloro-4-methylaminopyrimidine (III, EXAMPLE 1, 1.81 g). The mixture is stirred and heated under reflux for 23 hours, then is allowed to cool and concentrated under reduced pressure. The residue is partitioned between ethyl acetate and aqueous potassium bicarbonate, the phases separated and organic phase is concentrated to give a solid. The solid is crystallized from hexane to give the title compound, mp 100.5-103; NMR (CDCl3) 4.74, 3.51, 3.43, 2.81 and 1.9delta; CMR (CDCl3) 164.50, 161.92, 160.18, 70.78, 46.06, 45.85, 28.47, 25.44, 25.19delta. Alternatively, the title compound can be obtained by the reaction of 4-chloro-2,6-di-1-pyrrolidinylpyrimidine and methylamine (II) in pyridine in a pressure tube at 100, MS (M+) 247.

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, 32998-03-1, 2,6-Dichloro-N-methylpyrimidin-4-amine.

Reference:
Patent; The Upjohn Company; US5502187; (1996); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia