Tag: M.W:100-200

Application of 7226-23-5 ,Some common heterocyclic compound, 7226-23-5, molecular formula is C6H12N2O, 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.

EXAMPLE 62 {2-[3-Cyclopentyl-2-(4-trifluoromethanesulfonyl-phenyl)-propionylamino]-thiazol-4-yl}-acetic acid ethyl ester A solution of diisopropylamine (2.4 mL, 16.80 mmol) in dry tetrahydrofuran (7.5 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (2.5 mL) was cooled to -78 C. under nitrogen and then treated with a 2.5M solution of n-butyllithium in hexanes (6.7 mL, 16.80 mmol). The resulting reaction mixture was stirred at -78 C. for 30 min and then treated dropwise with a solution of 4-(trifluoromethylthio)phenylacetic acid (1.89 g, 8.00 mmol) in dry tetrahydrofuran (7.5 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (2.5 mL). The reaction mixture was allowed to stir at -78 C. for 55 min, at which time, a solution of iodomethylcyclopentane (1.85 g, 8.80 mmol) in a small amount of dry tetrahydrofuran was added dropwise. The reaction mixture was allowed to warm to 25 C. where it was stirred for 41 h. The reaction mixture was quenched with water and then concentrated in vacuo to remove tetrahydrofuran. The remaining aqueous phase was acidified to pH=2 with a 10% aqueous hydrochloric acid solution and then extracted with ethyl acetate (1*300 mL). The organic layer was washed with a saturated aqueous sodium chloride solution (1*100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-trifluoromethylsulfanyl-phenyl)propionic acid (1.47 g, 58%) as a cream solid: mp 69-71 C.; EI-HRMS m/e calcd for C15H17F3O2S (M+) 318.0901, found 318.0912.

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. 7226-23-5, 1,3-Dimethyltetrahydropyrimidin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffman-La Roche Inc.; US6610846; (2003); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 274-95-3 ,Some common heterocyclic compound, 274-95-3, molecular formula is C6H5N3, 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 C-1 (4 g) and sodium acetate (4.3 g) were dissolved in methanol (40 ml) into a 100 ml three-necked round bottom flask and then cooled to -10. Bromine (5.38 g) was slowly added dropwise. 1 M aqueous sodium sulfide solution (40 ml) was added, and the mixture was concentrated under reduced pressure. The by-product was extracted with ethyl acetate and water, and the resulting material was subjected to column separation using dichloromethane and methanol to obtain 3.2 g of the title compound

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. 274-95-3, Imidazo[1,2-a]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dae Joo Electronic Materials Co., Ltd.; Park Jeong-gyu; Jang Sun-uk; Lee Hyeon-seok; Kim Min-yeong; Jeon Yeong-min; (29 pag.)KR2017/126059; (2017); A;,
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.588-36-3, name is 4-Amino-5-hydroxymethyl-2-(methylthio)pyrimidine, molecular formula is C6H9N3OS, molecular weight is 171.22, as common compound, the synthetic route is as follows.SDS of cas: 588-36-3

c) 28 g (164 mmol) of 4-amino-2-methylthiopyrimidine-5-methanol were stirred in 500 ml of dichloromethane and treated with 150 g (1.7 mol) of manganese dioxide. The suspension was stirred for 24 hours and then filtered through a filter aid. The filtrate was evaporated to give 20.2 g (73%) of 4-amino-2-methylthiopyrimidine 5-carboxaldehyde as a pale yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,588-36-3, 4-Amino-5-hydroxymethyl-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Hoffmann-La Roche Inc.; US6150373; (2000); A;,
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. 4316-93-2, name is 4,6-Dichloro-5-nitropyrimidine, the common compound, a new synthetic route is introduced below. Formula: C4HCl2N3O2

General procedure: To a cooled to 5 C suspension of 4,6-dichloro-5-nitropyrimidine (6) (1.94 g, 10 mmol) and triethylamine (1.01 g, 10 mmol) in dichloromethane (10 mL), the corresponding ethyl N-alkylglycinate (10 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 30 min. The solution was then washed with water, the organic layer dried with Na2SO4 and evaporated under reduced pressure to dryness. The residue was purified by crystallization or column chromatography.

The synthetic route of 4316-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jakubkien?, Virginija; Linkus, Vytautas; ?ikotien?, Inga; Arkivoc; vol. 2018; 7; (2018); p. 154 – 171;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3934-20-1, 2,4-Dichloropyrimidine, 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, 3934-20-1, blongs to pyrimidines compound. COA of Formula: C4H2Cl2N2

A solution of 2,4-dichloropyrimidine (1.00 g, 6.71 mmol) and morpholine (0.59 mL, 6.81 mmol) in THF (25 mL) was charged with triethylamine (1 ,4 mL, 10.0 mmol) at 0 C. The reaction mixture was stirred at ambient temperature for 3 h. The reaction mixture was evaporated to dryness, the residue was taken up in CH2Cl2, and the organic layer was washed with water followed by brine; dried over sodium sulphate, filtered and concentrated. The residue was purified by combi-flash companion (silica gel, CH3OH/CH2CI2) to provide 4-(2-chloropyrimidm-4-yl)morpholine 417c (1.0 g, 70%) as a white solid. 1H NMR (300 MHz, CDCI3): delta 8.17 (d, J = 5 , 1 Hz, 1H), 6,53 (d, J = 5.1 Hz, I I I). 3.81 (t, ./ 4.5 Hz, 41 1 ). 3.75 (t, J =4.5 Hz, 4H); ESI+APCI MS m/z 200 [M + i | . A solution of 2-(5 -chloro-2,4-dimethoxyphenyl)-7-(piperazin-1-yl)imidazo[1 ,2-a]pyridine 301 (250 mg, 0.67 mmol) and NN-diisopropylethylamine (0.5 mL, 2.87 mmol) in DMF (7.5 mL) was charged with 4-(2-chloropyrimidin-4-yl)morpholine 417c (238 mg, 1.34 mmol). The reaction mixture was stirred at 100 C for 16 h. The reaction mixture was cooled to room temperature, suspended in water and stirred for 1 h. The precipitate was collected by filtration; the solid obtained was washed with water, dried under reduced pressure and purified by combi-flash companion (silica gel, CH3OH/CH2CI2). The product obtained was further triturated with methanol and filtered. The solids were washed with hexanes and dried to provide 4-(2-(4-(2-(5-chloro-2,4-dimethoxyphenyl)imidazo[1,2-a]pyridin-7-yl)piperazin-1-yl)pyrimidin-4-yl)morpholine 418c (20 mg, 5%) as an off-white solid. I NMR (300 MHz, DMSO- 6): 0 8.34 (d, ./ 10.0 Hz, i l l). 8.16 (s, I I I). 8.03 (s, ), 7.94 (d, J = 8.0 Hz, 1H), 6.87 (s, 1 H), 6.85 (s, 1 H), 6.71 (s, 1 H), 6.12 (d, J = 7,6 Hz, 4.01 (s, 3H), 3.93 (s, 3H), 3 ,82 (br s, 4H), 3.65 (br s, 4H), 3.53 (br s, All), 3,28 (br s, 4H); HPLC (Method 6) 97.4% (AUC), R = 1 1 .89 mm.; ESI+APCI MS m/z 536 [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,3934-20-1, its application will become more common.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); 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. SDS of cas: 3680-69-1

PREPARATION 155-bromo-4-chloro-1 /-/-pyrrolo[2,3-c/]pyriA mixture of 4-chloro-1 H-pyrrolo[2,3-c ]pyrimidine (10 g, 65.1 mmol) in CH2CI2 (400 mL) at 25 C was treated with NBS (13.91 g, 78 mmol) and stirred for 30 min before being concentrated. The resulting brown solid was triturated with water (-500 mL) and after drying, was triturated with EtOAc to afford the title compound (12.4 g, 73.7%) as a tan solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 12.99 (br. s, 1 H), 8.64 (s, 1 H), 7.97 (d, J = 2.76 Hz, 1 H); MS (m/z) 232.9 (M+H+).

The synthetic route of 3680-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; HAMMOND, Marlys; KALLANDER, Lara, S.; LAWHORN, Brian, Griffin; PHILP, Joanne; SARPONG, Martha, A.; SEEFELD, Mark, Andrew; WO2011/149827; (2011); A1;,
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Pyrimidine – Wikipedia

Application of 106157-82-8, Adding some certain compound to certain chemical reactions, such as: 106157-82-8, name is 1-(2-Aminopyrimidin-4-yl)ethanone,molecular formula is C6H7N3O, 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 106157-82-8.

Example 2 1- (2-AMINOPYRIMIDIN-4-YL)-2-BROMOETHANONE hydrobromide The title compound (a) was prepared by working as described in J. Het. Chem. 1985,22, 1723. A mixture of 3,3-dimethoxy-2-butanone (25 9, 189.16 MMOL) and N, N-DIMETHYLFORMAMIDE DIMETHYLACETAL (22.5 g, 189.16 MMOL) were stirred at 110C for 30 hours and then distilled (115C, 1 mmHg) thus obtaining 1-(DIMETHYLAMINO)-4, 4-DIMETHOXYPENT-1-EN-3-ONE, as a yellow solid (27.3 G, 146 mmol, 77%). Onto a solution of sodium (3.48 g, 151.67 MMOL) in anhydrous ethanol (400 mL), solid guanidine hydrochloride (14.5 G, 151.67 MMOL) was added at r. t. , to give a white suspension into which a solution of 1-(DIMETHYLAMINO)-4, 4-DIMETHOXYPENT-1-EN-3-ONE (28.4 g, 151.67 MMOL) in anhydrous ethanol (50 mL) was added. The mixture was refluxed for 19 hours. After cooling, the precipitate was filtered and washed with ethanol and with plenty of water, thus obtaining a white solid (8.56 G). The ethanolic solutions were concentrated to dryness, taken up with boiling ethyl acetate (1000 mL), filtered while hot and then cooled to yield a second crop. Total amount of 4- (1, 1-DIMETHOXYETHYL) PYRIMIDIN-2-AMINE : 17.66 G, 63. 5%. A solution of the said amine (17. 5 G, 95.5 MMOL) in formic acid was stirred at r. t. for 6 hours and concentrated to dryness and the residue was stirred in ethanol (50 mL) and then filtered thus obtaining 1- (2-aminopyrimidin-4-yl) ethanone (9.2 g, 70%). To a solution of 1- (2- aminopyrimidin-4-yl) ethanone (412 mg, 3 MMOL) in glacial acetic acid (1 mL) and 48% aq. HBr (0.3 mL), bromine (0.153 mL) in acetic acid (0.4 mL) was added and the resulting orange solution was stirred at r. t. for 15 hours. After diluting with ethyl acetate (15 mL) the precipitate was filtered and washed with ethyl acetate thus affording the title compound as a whitish solid (580 mg, 65%).

According to the analysis of related databases, 106157-82-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACIA & ITALIA S.p.A.; WO2005/14572; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 7355-55-7, 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 7355-55-7 as follows.

A 50 cm3 round-bottomed flask containing a stirring bar was charged with 2- amino-3W-pyrrolo[2,3-d]pyrimidin-4(7A )-one (2.00 g, 13.33 mmol). The flask was fitted with a septum and placed under an Ar atmosphere. Freshly distilled pyridine (20.00 cm3) was added via syringe and the resulting suspension cooled on ice. The solution was allowed to equilibrate at this temperature (ca. 5 min) and then octanoyl chloride (6.80 cm3, 39.99 mmol) was added dropwise. The resulting suspension was heated at 85 C for 30 min. After cooling to room temperature 6.5% ethanolic ammonia (60 cm3) was added and the resulting suspension stirred at room temperature overnight. The precipitate of product was removed via vacuum filtration and washed with ethanol followed by diethyl ether to yield the desired product (2.56 g, 70%) pure as a yellow solid, m.p. > 300 C (decomposition). Procedure based on Akimoto et al. 1986 and Akimoto et al. 1988. deltaEta (400 MHz, DMSO-de): 0.86 (3H, t, J 5.1), 1.26 (8H, m), 1.58 (2H, app. quintet), 2.01 (1H, br s, NH), 2.43 (2H, t, J 5.1), 6.40 (1H, d, J 2.0), 7.01 (1H, d, J 2.0), 11.43 (1H, br s, NH), 11.67 (1H, br s, NH) HRMS (m/z ESI ) : Found : 275.1517 ([M-H]” C14H 19N4O2; Requires: 275.1508)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7355-55-7, its application will become more common.

Reference:
Patent; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH, NEAR DUBLIN; SOUTHERN, John, Michael; CONNON, Stephen, J.; (37 pag.)WO2016/50804; (2016); 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. 74356-36-8, name is 2,4-Dimethyl-pyrimidine-5-carboxylic acid. A new synthetic method of this compound is introduced below., COA of Formula: C7H8N2O2

Reference Example 78 2,4-dimethylpyrimidine 2,4-Dimethyl-5-pyrimidinecarboxylic acid was heated at 160C for 4 hrs. The reaction mixture was distilled under atmospheric pressure to give the title compound (17 g, yield 49%). boiling point 152-153C. 1H-NMR(CDCl3)delta: 2.50 (3H, s), 2.70 (3H, s), 6.98 (1H, d, J= 5.1Hz), 8.49 (1H, d, J= 5.1Hz).

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, 74356-36-8, 2,4-Dimethyl-pyrimidine-5-carboxylic acid.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1364949; (2003); 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. 2434-56-2, name is 4,6-Diaminopyrimidine, the common compound, a new synthetic route is introduced below. name: 4,6-Diaminopyrimidine

Compound 4,6-diaminopyrimidine 21a (70.0 mg, 0.6 mmol), 4-chloro-2-fluoropyridine (65.0 mg, 0.5 mmol) andN,N-Dimethylacetamide (5.0 mL) was added, and cesium carbonate (327.0 mg, 1 mmol) was added at room temperature, and stirred at 110 C for 3 hours.The mixture was quenched with 20 mL of water and the organic phase was separated. The aqueous phase was extracted with dichloromethane (15 mL¡Á2)Wash with saline (50 mL ¡Á 2). The organic phase is dried over anhydrous sodium sulfate, and the desiccant is removed by filtration, and the residue is evaporated to dryness.Purification by preparative silica gel plate (dichloromethane/methanol = 10:1) gave the desired product 4-(4-chloropyridin-2-yl)amino-6-aminoPyrimidine 21b (18.0 mg, 0.08 mmol, yellow solid). Yield: 16%.

The synthetic route of 2434-56-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Tianyinjianhua Pharmaceutical Technology Co., Ltd.; Kong Xianglong; Zhou Chao; Zheng Zhixiang; (105 pag.)CN109020957; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia