Tag: M.W:200-300

Reference of 2972-52-3, 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. 2972-52-3, name is 2,4-Dichloro-5-pyrimidinecarbonyl chloride, molecular formula is C5HCl3N2O, 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.

Example 3 Synthesis of 5-carboxyamide-2,4-dichloropyrimidine To a 2 L round bottom flask equipped with water condenser and a CaCl2 drying tube, 2,4-dihydroxypyrimidine (25 g, 0.16 mole) was added to PCl5 (117 g, 0.56 mole), and POCl3 (250 ml, 2.6 mole). The mixture was heated at 115 C. overnight to give a clear, slightly light yellow solution. The mixture was cooled to room temperature, and was concentrated under reduced pressure to give pale yellowish oil. To this oil, anhydrous 1,4-dioxane (300 ml) was added and the mixture was cooled to 0 C. in an ice/water bath. 35 ml of NH3 in water (28%) was added dropwise to the mixture with stirring, temperature was kept below 5 C. The mixture changed from clear to white with precipitate forming, and was stirred for 1 hour at 0 C., reaction was followed by TLC (1:1 Hexanes:Ethyl Acetate). Ethyl acetate (700 ml) and water (500 ml) were added to the mixture, the 2 layers were separated. The organic layer was dried with Na2SO4, and filtered. The solution was concentrated under reduced pressure to give a light yellow solid. This light yellow solid was sonicated with methylene chloride (200 ml), and filtered to give a pale yellow solid (16 g). This pale yellow solid was dissolved into ethyl acetate (1.5 L) and washed with sat. NaHCO3 (500 ml). The organic layer was dried with Na2SO4, filtered, and concentrated under reduced pressure to give 13.1 g of product as a white solid (44% yield). 1H NMR (DMSO-d6, 300 MHz): delta 8.86 (s, 1H), 8.14 (bs, 1H), 8.02 (bs, 1H).

According to the analysis of related databases, 2972-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Holland, Sacha; Kolluri, Rao; Alvarez, Salvador; Duncton, Matthew; Singh, Rajinder; Zhang, Jing; Masuda, Esteban; US2012/22092; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 33097-11-9 ,Some common heterocyclic compound, 33097-11-9, molecular formula is C6H4Cl2N2OS, 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.

General procedure: To a stirred solution of aldehyde 1 (1.0mmol, 1equiv) in 3mL DMF was added enamine 2 (1.15equiv) followed by addition of a few drops of satd ethereal HCl. (0027) Except for 6d: Mixture was stirred at ambient temperature for period of time indicated in Table 1. After removing of solvent (50C/5 Torr) the residue was stirred with water (10mL) for 1h, crystals were filtered and dried at 110C/5 Torr to give compound 6 with purity?94%. Recrystallization from DMF can be used for purification, if necessary. (0028) For 6d: After stirring for 20h the additional portion of enamine 4d (0.15equiv) was added and the mixture was left at ambient temperature for 4 days. After removing of solvent (50C/5 Torr) the residue was dissolved in CHCl3 (30mL), washed with water, satd NaHCO3 and brine. Compound 6d was isolated using column chromatography on silica (EtOAc-nHexane 1:1, Rf?0.25).

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. 33097-11-9, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chizhova, Maria E.; Bakulina, Olga Yu.; Ivanov, Alexander Yu.; Lobanov, Pavel S.; Dar’in, Dmitrii V.; Tetrahedron; vol. 71; 36; (2015); p. 6196 – 6203;,
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. 62208-68-8, name is Benzofuro[3,2-d]pyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C10H6N2O3

In a 1000 mL round flask, a mixture of Compound B-1 (49.4 g, 0.24 mol) and phosphorus oxychloride (720 mL) was stirred at reflux for 7.5 h 7. The reaction mixture is cooled to room temperature and poured into ice water with vigorous stirring to precipitate the precipitate.Generated. The reaction obtained therefrom was filtered to give Compound B (45.1 g, 77% yield, white solid).

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, 62208-68-8, Benzofuro[3,2-d]pyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; LG Chem, Ltd.; Han Su-jin; Lee Jeong-ha; Lee Dong-hun; Jang Bun-jae; Jeong Min-u; Park Seul-chan; (56 pag.)KR2019/113662; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
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Synthetic Route of 65269-18-3, 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 65269-18-3 as follows.

Example 15 9-[2-Chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-2-methoxy-7,9-dihydro-8H-purin-8-one A mixture of ethyl 4-chloro-2-methoxypyrimidine-5-carboxylate (0.22 g), 2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyaniline hydrochloride (0.4 g) and N,N-diisopropylethylamine (0.37 mL) in acetonitrile (3 mL) was heated at reflux for 1.5 hours. The reaction mixture was poured into water. To the mixture was added ethyl acetate, and the insoluble material was collected by filtration. The collected solids were washed with water and ethyl acetate, and dried under reduced pressure to give ethyl 4-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenylamino]-2-methoxypyrimidine-5-carboxylate (91 mg). To this material were added methanol (2 mL) and 1 mol/L aqueous sodium hydroxide solution (0.9 mL), and the mixture was stirred at 50C for 1 hour. To the mixture was added tetrahydrofuran (1 mL), and the mixture was stirred at 50C for 1 hour. The reaction mixture was cooled to room temperature. To the mixture was added 1 mol/L hydrochloric acid (1.0 mL), and the mixture was stirred for 30 minutes. The precipitated crystals were collected by filtration. The collected crystals were washed with water and diethyl ether, and dried under reduced pressure to give 4-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxy-phenylamino]-2-methoxypyrimidine-5-carboxylic acid (57 mg). To this material were added 1,4-dioxane (1 mL), triethylamine (0.049 mL) and diphenylphosphoryl azide (0.026 mL), and the mixture was stirred at room temperature for 1 hour, and then heated at reflux for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 1/1 – 1/5). The product was suspended in a mixed solvent (n-hexane/ethyl acetate = 1/1), and collected by filtration. The collected material was washed with the same solvent, and dried under reduced pressure to give the title compound (20 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,65269-18-3, its application will become more common.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP2143724; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 63558-65-6, 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. 63558-65-6, name is 4-Chloro-5-iodopyrimidine, molecular formula is C4H2ClIN2, 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.

EXAMPLE 5 Preparation of 4-chloro-5-phenylethynylpyrimidine A mixture of 2.1 g of 4-chloro-5-iodopyrimidine, 10 mL of triethylamine, 1.2 mL phenylacetylene, 80 mg copper iodide and 160 mg of dichlorobis(triphenylphosphine was stirred at room temperature for 18 hours. The mixture was diluted with dichloromethane and evaporated in vacuo. The residue was redissolved in a few mL of dichloromethane, 10 mL of triethylamine added and the mixture heated at reflux for one hour. The heterogeneous mixture was evaporated in vacuo and the residue obtained was partitioned between water and dichloromethane. A gelatinous precipitate which formed on shaking the two layers was filtered off, enabling separation of the two layers. The organic extracts were dried over sodium sulfate, filtrated and evaporated in vacuo to yield 2.5 g of a dark brown syrup. The syrup was purified by column chromatography on silica gel, twice, eluding with hexanes, 1:1 hexanes/dichloromethane, dichloromethane and finally ethyl acetate. Like fractions from dichloromethane elution were pooled, obtaining 350 mg of the product, 5-phenylethynyl-4-chloropyrimidine as an oil which solidified to white rosettes.

According to the analysis of related databases, 63558-65-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beauchamp, Lilia M.; Krenitsky, Thomas A.; Kelley, James L.; US2004/87789; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1032452-86-0, 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole, 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, Computed Properties of C13H10ClN3, blongs to pyrimidines compound. Computed Properties of C13H10ClN3

60 g (246 mmol) of Intermediate 2 was dissolved in 500 mL of 1,4-dioxane, and 45.8 g (246 mmol) of 4-fluoro-2-methoxy-5-nitroaniline was sequentially added to the above mixed solution. 50.8 g (295 mmol) of p-toluenesulfonic acid, heated to 85 C and stirred for 3 h. After completion of the reaction, the mixture was cooled to room temperature, and 10 mL of dilute aqueous ammonia was added to the reaction mixture to quench the reaction. The mixed solution was added dropwise to 500 mL of water, stirred at room temperature for 3 hours, filtered, and the filter cake was dried to give 93.6 g of pale yellow-green solid.The yield is 96.7%.

The synthetic route of 1032452-86-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangxi Science and Technology Normal University; Zhu Wufu; Zheng Pengwu; Zhao Bingbing; Xu Shan; Xiao Zhen; Hu Xiaohan; Zhou Zhihui; He Jie; Lai Luogen; Yang Qi; Tian Fajuan; (31 pag.)CN109280048; (2019); A;,
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. 39551-54-7, name is 2,4-Dichloropyrido[3,2-d]pyrimidine, molecular formula is C7H3Cl2N3, 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. Formula: C7H3Cl2N3

A mixture of 2,4-dichloropyrido[3,2-d]pyrimidine (150 mg, 749.91 mupiiotaomicron, 1 eq), 4,5,6,7- tetrahydro-lH-indol-5-amine (113.48 mg, 749.91 muiotaetaomicron, 1 eq) and DIEA (387.68 mg, 3.00 mmol, 522.48 mu., 4 eq) in z-PrOH (10 mL) was stirred at 55 C for 2 h. The reaction mixture was concentrated to yield the residue which was purified on silica gel column chromatography (from PE/EtOAc = 3/1 to 1/1, TLC: PE/EtOAc = 1/1, Rf = 0.50) to yield 2-chloro-N-(4,5,6,7-tetrahydro- lH-indol-5-yl)pyrido[3,2-d]pyrimidin-4-amine (120 mg, 397.52 muiotaetaomicron, 53.0% yield, 99.3% purity) as a yellow solid. 1H MR (400 MHz, CDCb) S ppm 8.64 (dd, J= 1.5, 4.3 Hz, 1H), 8.01 (dd, J = 1.5, 8.5 Hz, 1H), 7.85 (s, 1H), 7.64 (dd, J= 4.3, 8.3 Hz, 1H), 7.44 (d, J= 8.5 Hz, 1H), 6.70 (t, J = 2.6 Hz, 1H), 6.04 (t, J= 2.6 Hz, 1H), 4.80-4.70 (m, 1H), 3.10 (dd, J= 5.3, 15.3 Hz, 1H), 2.99-2.45 (m, 3H), 2.24-2.08 (m, 2H); ES-LCMS m/z 300.1 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 39551-54-7.

Reference:
Patent; KYN THERAPEUTICS; CASTRO, Alfredo C.; EVANS, Catherine Anne; (632 pag.)WO2018/195397; (2018); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 6693-08-9, Adding some certain compound to certain chemical reactions, such as: 6693-08-9, name is 2,4,6-Trichloro-5-fluoropyrimidine,molecular formula is C4Cl3FN2, 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 6693-08-9.

1 1(S)-5-Fluoro-W4-(1 -(5-fluoropyridin-2-yl)ethyl)-yV2-(2-methoxypyridin-3-yl)-6- morpholinopyrimidine-2,4-diamine a) 4-(2,6-Dichloro-5-fluoropyrimidin-4-yl)morpholineA solution of morpholine (1 .5 mL, 17.05 mmol) in ethanol (25 mL) was added to a cooled (-20 C) solution of 2,4,6-trichloro-5-fluoropyrimidine (3.00 g, 14.93 mmol) in ethanol (150 mL) and the resulting mixture was stirred at -20 C for 30 minutes and at ambient temperature for 3 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between water and methylene chloride. The organic layer was separated, dried and the solvent evaporated under reduced pressure. The resulting white solid was triturated with ethanol, then filtered and dried to give the title compound (2.0 g, 53%).LRMS (m/z): 252/254 (M+1 )+.1H-NMR delta (CDCIs): 3.77-3.80 (m, 4H), 3.82-3.85 (m, 4H).

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. 6693-08-9, 2,4,6-Trichloro-5-fluoropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; BACH TANA, Jordi; PAGES SANTACANA, Lluis Miquel; WO2013/17461; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 32779-38-7 ,Some common heterocyclic compound, 32779-38-7, molecular formula is C4H2ClIN2, 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 A6. General experimental for the Negishi cross-couplingGeneral Scheme:Pd(PPh3)4 R99aZnBr + Ra 9a9Bb.l p99ap99b Representative Scheme:To a solution of tetrakis(triphenylphosphine)palladium (0.05 equiv) in THF was added the organozinc reagent (e.g., pyridin-2-ylzinc bromide, 2 equiv) at 15 C under N2. Then, a solution of aryl iodine (e.g., 2-chloro-5-iodopyrimidine, 1 equiv) in THF was added. The reaction mixture was stirred at room temperature for 3 h. The mixture was poured into ¾0 and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2S04. After filtration and concentration, the crude product was purified by silica-gel column to give the C-C coupling product (e.g., 2-chloro-5- (pyridin-2-yl)pyrimidine).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,32779-38-7, its application will become more common.

Reference:
Patent; HEFFERNAN, Michele, L., R.; HARDY, Larry, Wendell; WU, Frank, Xinhe; SARASWAT, Lakshmi, D.; SPEAR, Kerry, L.; WO2012/170845; (2012); A2;,
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 151266-23-8, name is 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. name: 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

[00129] To a mixture of 3-iodo-1 H-pyrazolo[3,4-d]pyrimidin-4-amine (1.044 g, 4 mmol), (4-phenoxyphenyl)boronic acid (0.94 g, 4.4 mmol, 1.1 eq), PdCl2(dppf) (0.29 g, 0.4 mmol, 0.1 eq) and Na2CO3 (0.89 g, 8.4 mmol, 2.1 eq) in a 40 ml reaction vial under vacuum, 25 mL of H20/THF (1 :4) is added via a syringe. The mixture is refilled with N2 and heated to 110 C overnight. TLC showed that the reaction is almost completed. Then solvent is evaporated and the residue is suspended in 200 mL (15% THF/EtOAc) and washed with water, brine, dried over Na2SO4, filtered, and evaporated. The residue is purified with a 50 g silica gel cartridge by Combi-flash (0-10% gradient of methanol in DCM to afford 513 mg of 3-(4-phenoxyphenyl)-1 H-pyrazolo[3,4-d]pyrimidin-4-amine. 1HNMR (300 MHz, DMSO-d6): delta 8.22 (s, 1 H), 7.66 (d, 2 H), 7.43 (t, 2 H), 7.10- 7.23 (m, 5 H).

With the rapid development of chemical substances, we look forward to future research findings about 151266-23-8.

Reference:
Patent; BETA PHARMA CANADA INC.; WANG, Zhaoyin; LI, Lianhai; WANG, Zhigang; WO2013/113097; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia