Day: November 9, 2020

74-69-1, 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 74-69-1 as follows.

General procedure: In the vessel of a microwave reactor, 12 (400 mg, 1.13 mmol), 2-aminopyridine (318 mg, 3.38 mmol), Pd2(dba)3 (51.6 mg,56.4 lmol), 2-dicyclohexylphosphino-20,40,60-triisopropyl-1,10-biphenyl (26.9 mg, 56.4 lmol), and K2CO3 (312 mg, 2.25 mmol)were suspended in t-BuOH (3 mL). The vessel was then sealed,and the mixture was reacted at 130 C for 1 h under microwaveirradiation. After cooling to room temperature, the mixture wasextracted with CHCl3/MeOH (4:1), and washed with brine. Theorganic layer was separated, dried over MgSO4, and concentratedunder reduced pressure. The residue was purified by NH silicagel column chromatography (CHCl3/MeOH = 100:0 to 90:10) togive the title compound (362 mg, 78%). 1H NMR (400 MHz,DMSO-d6) d: 1.27-1.38 (2H, m), 1.41 (9H, s), 1.95-2.02 (2H, m),2.96-3.10 (2H, m), 3.43-3.53 (1H, m), 3.80-3.88 (2H, m), 6.83-6.87 (1H, m), 7.07 (1H, br), 7.22 (1H, s), 7.62-7.66 (2H, m), 7.80(1H, br), 8.20-8.22 (1H, m), 8.40 (1H, s), 8.70 (1H, d, J = 7.2 Hz),9.47 (1H, s). MS (ESI) m/z: 413 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 74-69-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Nakajima, Yutaka; Aoyama, Naohiro; Takahashi, Fumie; Sasaki, Hiroshi; Hatanaka, Keiko; Moritomo, Ayako; Inami, Masamichi; Ito, Misato; Nakamura, Koji; Nakamori, Fumihiro; Inoue, Takayuki; Shirakami, Shohei; Bioorganic and Medicinal Chemistry; vol. 24; 19; (2016); p. 4711 – 4722;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

A common compound: 720-01-4, name is Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate,molecular formula is C8H6ClF3N2O2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 720-01-4

Example 18 ETHYL 4-HYDRAZINO-2-TRIFLUOROMETHYLPYRIMIDINE-5-CARBOXYLATE A solution of ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate (0.20 g, 0.79 mmol), hydrazine (0.18 g, 6.0 mmol) and THF was stirred for 1 h at room temperature. The solution was filtered and dried to give the title compound in a 96% yield; 1 H NMR (CDCl3) delta 9.26 (bs, 1H), 8.90 (s, 1H), 4.40 (q, 2H), 4.24 (bs, 2H), 1.41 (t,3H).

With the rapid development of chemical substances, we look forward to future research findings about 720-01-4.

Reference:
Patent; Signal Pharmaceuticals, Inc.; US5935966; (1999); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

90213-66-4, 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 90213-66-4, name is 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

1.0 g of 2,4-dichloro-7H-pyrrole [2,3-d]pyrimidine was dissolved in 50 mL of dichloromethane under ice bath. To the above mixed solution, 1.06 g of p-toluenesulfonyl chloride, 1.08 g of triethylamine, and 0.019 g of 4-dimethylaminopyridine were slowly added. The mixed solution was stirred at room temperature for 5 h. After the reaction was completed, 150 mL of dichloromethane was poured into the above solution, and the organic phase was washed three times with 100 mL of each of water, aqueous citric acid and brine; The organic phase was dried over anhydrous magnesium sulfate (MgSO4). Recrystallization from petroleum ether gave 1.6 g of white pure product. The yield was 89%.

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 90213-66-4, 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Shandong University; Zhang Yingjie; Liang Xuewu; Xu Wenfang; (47 pag.)CN108864057; (2018); A;,
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. 591-55-9, name is 5-Aminopyrimidine. A new synthetic method of this compound is introduced below., 591-55-9

General procedure: Ethyl 2-[(2-fluorophenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate. Diethyl malonate (1.0 mL, 6.6 mmol) was addeddropwise to a solution of sodium hydride (60% w/w in oil, 317 mg,7.9 mmol) in anhydrous tetrahydrofuran (12 mL) that was cooledwith ice bath. The mixture was heated at reflux for 6 min. Aftercooling with ice bath, the reaction mixture was treated dropwisewith chloroacetyl chloride (0.58 mL, 7.2 mmol) and stirred in the icebath for 1 h, and then stirred at 45 C for 1 h. The reaction mixturewas cooled in the ice bath again, and then 2-fluoroaniline (0.76 mL,7.9 mmol) was added dropwise. After stirring at ambient temperaturefor 17 h, the reaction mixture was heated at reflux for 2.5 h.The reaction mixture was allowed to cool to ambient temperature,diluted with aqueous saturated sodium bicarbonate solution, andextracted with ethyl acetate twice and with chloroform. Theorganic layerwaswashed with brine, dried over sodium sulfate andconcentrated. The residue was triturated with ethanol-hexane toafford the title compound as a pale yellow solid (0.58 g, 33%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,591-55-9, 5-Aminopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Irie, Takayuki; Asami, Tokiko; Sawa, Ayako; Uno, Yuko; Hanada, Mitsuharu; Taniyama, Chika; Funakoshi, Yoko; Masai, Hisao; Sawa, Masaaki; European Journal of Medicinal Chemistry; vol. 130; (2017); p. 406 – 418;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

302964-08-5, 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. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, molecular formula is C16H13Cl2N5OS, 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.

2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, 7(1.00 g, 2.54 mmol), piperazine (2.19 g, 25.4 mmol),N,N-diisopropylethylamine (0.84 mL, 5.07 mmol) was dissolved in anhydrous 1,4-dioxane (30 ml) and refluxed for 12 h.The oil obtained by distillation under reduced pressure was washed with water / methanol, methanol / ether to give an off white solid.The crude product was recrystallized from diethyl ether to give compound 8 (0.82 g, 73%)

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. 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; China Pharmaceutical University; You Qidong; Jiang Zhengyu; Wang Yan; Jin Yuhui; Lu Mengchen; Xu Xiaoli; Guo Xiaoke; (21 pag.)CN109761970; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

1820-81-1, 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. 1820-81-1, name is 5-Chlorouracil, molecular formula is C4H3ClN2O2, 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.

General procedure: A mixture of pyrimidine (1mmol) and ammonium sulfate (0.10mmol) in HMDS (1.5 ml) was refluxed until clear solution was obtained (3h). Then alkyl bromide (2mmol, 0.22ml), KI (0.5mmol, 83mg) and acetonitrile (2.5ml) were added. Reaction mixture was heated at 90C for 5h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with dichloromethane and evaporated to dryness. The residue was purified by flash chromatography eluting with MeOH/dichloromethane (1/10).

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. 1820-81-1, 5-Chlorouracil, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mansouri, Az-Eddine El; Zahouily, Mohamed; Lazrek, Hassan B.; Synthetic Communications; (2019);,
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. 5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, 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. 5750-76-5

Intermediate 1 2,5-dichloro-N-(5-methyl-lH-pyrazol-3-yl)pyrimidin-4- amine [0078] A mixture of 5-methyl-lH-pyrazol-3-amine (3.00 g, 30.9 mmol), 2,4,5- trichloropyrimidine (5.67 g, 30.9 mmol, 1 equiv.) and Na2CO3 (3.60 g, 34.0 mmol, 1.1 equiv.) in EtOH (100 mL) was heated at 40 0C for 24 h. The solvent was removed in vacuo. The resulting residue was partitioned between EtOAc (350 mL) and water (100 mL). The EtOAc layer was washed with water (3x), saturated aqueous NaCl (Ix) and dried over Na2SO4. The resulting EtOAc solution was concentrated in vacuo, providing the product 2,5-dichloro-N-(5-methyl-lH-pyrazol-3-yl)pyrimidin-4-amine; ESMS m/z 244.0 (M + H+).

The chemical industry reduces the impact on the environment during synthesis 5750-76-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; IRM LLC; WO2009/158431; (2009); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

4595-59-9 , The common heterocyclic compound, 4595-59-9, name is 5-Bromopyrimidine, molecular formula is C4H3BrN2, 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: In a 5 mL flask, aryl halide (1 mmol), alkyl halide (1.1 mmol),thiourea (91 mg, 1.2 mmol), CuFe2O4(12 mg, 5 mol%), K2CO3(552 mg, 4.0 mmol), H2O (0.3 mL), and PEG (2 mL) were added and stirred at 80-100C for the appropriate reaction time. After completion of reaction, the mixture was cooled to room temperature and washed with 5 mL H2O and 10 mL EtOAc. Then,after separation and evaporation of organic solvent, the crude thioethers, were purified by flash column chromatography on silica gel eluted with the appropriate mixture of (EtOAc/n-hexane).

According to the analysis of related databases, 4595-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gholinejad, Mohammad; Karimi, Babak; Mansouri, Fariborz; Journal of Molecular Catalysis A: Chemical; vol. 386; (2014); p. 20 – 27;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

591-55-9 , The common heterocyclic compound, 591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, 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.

To a solution of (2,6-dimethylpyridin-4-yl)(4-(l-(/ra5-4-hydroxycyclohexyl)-6- (methylsulfonyl)-liT-pyrazolo[3,4-d]pyrimidin-3-yl)-5,6-dihydropyridin-l(2H)-yl)methanone (100 mg, 0.20 mmol) in THF (10 mL) was added a 1.0 M solution of lithium bis(trimethylsilyl)amide (LiHMDS) in THF (0.78 mL, 4.0 equiv.) at -70 C followed by slow addition of pyrimidin-5-amine (37 mg, 0.39 mmol). The reaction mixture was stirred at -70 C. After complete conversion, the reaction mixture was quenched with water (10 mL), extracted with EtOAc (3 x 10 mL), dried (Na2S04), and concentrated. The residue was purified by column chromatography with ethyl acetate/hexane and methanol/water to provide (2,6- dimethylpyridin-4-yl)(4-(l-(/ra5-4-hydroxycyclohexyl)-6-(pyrimidin-5-ylamino)-liT- pyrazolo[3,4-i/]pyrimidin-3-yl)-5,6-dihydropyridin-l(2i7)-yl)methanone (13 mg, 12%) as a pale solid.

According to the analysis of related databases, 591-55-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WANG, Xiaodong; FRYE, Stephen; (113 pag.)WO2019/222509; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

696-82-2, 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 696-82-2, name is 2,4,6-Trifluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2,4,6-trifluoropyrimidine (278 mg, 2.07 mmol) in Et20 (10 mL) is cooled to -20 C and is treated, dropwise, with a solution of tert-butyl 4-[[4-[(1S)-1- aminoethyllphenyllmethyllpiperazine-1-carboxylate (600 mg, 1.88 mmol) in Et20 (10 mL). The resulting mixture is stirred at -20 C for 1 hour and is then allowed to warm to room temperature and is stirred overnight. The solids are removed by filtration and arewashed with additional Et20. The filtrate is washed with water, using a small portion of NaC1 additive to reduce emulsification, and the aqueous layer is back-extracted with Et20 (lx) and CH2C12 (lx). The combined organic extracts are then dried (Na2SO4), filtered,and concentrated to give a crude product that is purified by silica gel chromatographyeluting with 20-60% EtOAc/hexanes to give the title compound as a pale yellow oil (606 mg, 1.40 mmol, 74%). ES/MS (mlz): 434 (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 696-82-2, 2,4,6-Trifluoropyrimidine.

Reference:
Patent; ELI LILLY AND COMPANY; LUMERAS AMADOR, Wenceslao; BAUER, Renato A.; BOULET, Serge Louis; BURKHOLDER, Timothy Paul; GILMOUR, Raymond; HAHN, Patric James; CARBALLARES MARTIN, Santiago; RANKOVIC, Zoran; (80 pag.)WO2017/213910; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia