Category: pyrimidines

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. 1202759-91-8, name is N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine. A new synthetic method of this compound is introduced below., Application In Synthesis of N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine

Weigh 24mg pentafluorobenzoic acid, 42mg HATU, 15mg HOAT in a 25ml round bottom flask and add 0.8mlDCM, 0.2 ml of DMF and 33 mul of DIEA as solvents were stirred at room temperature for about 10 minutes. 37 mg of the A1 intermediate was added to the reaction system. After stirring at room temperature for about 1 hour, 100 ml of saturated aqueous sodium bicarbonate solution was added, followed by 15 ml of DCM. The mixture was extracted 3 times and the resulting organic phase was dried under reduced pressure. The residue was applied to a silica gel column with DCM_MeOH=70:1 (v/v) to give 29 mg of the compound represented by Formula III-3 in 52% yield.

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, 1202759-91-8, N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine.

Reference:
Patent; Tsinghua University; Rao Yu; Liu Wanli; Yang Maojun; Sun Yonghui; (22 pag.)CN107973754; (2018); A;,
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Related Products of 14080-23-0, 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. 14080-23-0, name is 2-Cyanopyrimidine, molecular formula is C5H3N3, 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.

Step A: Preparation of methylpyrimidine-2-carboxylate: HCl gas was bubbled through methanol (“MeOH”, 700 mL) at a temperature of 0 C. for 30 minutes to give a saturated solution. Pyrimidine-2-carbonitrile (21.585 g, 205.38 mmol) was added to this solution, and the mixture was stirred at room temperature for 16 hours and then at a temperature ranging from about 40 to about 50 C. for 3 hours. The reaction mixture was concentrated, and the residue was dissolved in water. The pH was adjusted to about 7.0 using solid NaHCO3. The aqueous layer was extracted with 20% isopropyl alcohol (“iPrOH”)/dichloromethane (“DCM”) (3*). The combined organics were dried over sodium sulfate, filtered and concentrated under vacuum to give the desired product as white solids (23.0 g, 81%). 1H NMR (400 MHz, CDCl3) delta 8.97-8.96 (d, J=4.7 Hz, 2H), 7.53-7.50 (t, J=4.7 Hz, 1H), 4.09 (s, 3H).

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 14080-23-0, 2-Cyanopyrimidine.

Reference:
Patent; Array Biopharma, Inc.; US2010/63066; (2010); A1;,
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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. 149849-94-5, name is Methyl 2-chloropyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below., Recommanded Product: 149849-94-5

To a solution of 2-oxa-6-azaspiro[3.3]heptane hemioxalate (1.04 g) in dioxane (10 mL) was added triethylamine (1.55 mL) and the reaction mixture was stirred for 10 minutes at ambient temperature. Methyl 2-chloropyrimidine-4-carboxylate (500 mg) was added and the reaction mixture was stirred at 80 C for 6 hours in a Biotage Initiator microwave unit. To the reaction mixture was added water and the aqueous phase was extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude product was used without any further purification in the next step. MS (ESI) m/z 230.4 (M+H)+

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Reference:
Patent; ABBVIE INC.; ABBVIE DEUTSCHLAND GMBH & CO. KG; BRAJE, Wilfried; DOHERTY, George; JANTOS, Katja; JI, Cheng; JUDD, Andrew; KUNZER, Aaron; MASTRACCHIO, Anthony; SONG, Xiaohong; SOUERS, Andrew; SULLIVAN, Gerard; TAO, Zhi-Fu; LAI, Chunqui; KLING, Andreas; POHLKI, Frauke; TESKE, Jessc; WENDT, Michael; BRADY, Patrick; WANG, Xilu; PENNING, Thomas; MICHAELIDES, Michael; (448 pag.)WO2019/35927; (2019); A1;,
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Related Products of 5767-35-1, 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.5767-35-1, name is 4-Chloro-6-hydrazinopyrimidine, molecular formula is C4H5ClN4, molecular weight is 144.56, as common compound, the synthetic route is as follows.

Intermediate-21 A (13.0mL, 69.2mmol) and 1N 26 HCl (10mL) were added dropwise in the solution of 27 C (10.0g, 69.2mmol) in 23 ethanol (100mL) at 0-5C and was stirred for 1h. Completion of reaction was confirmed on TLC after 1h. Then reaction mixture was poured on ice water to afford crude product. Filtration and recrystallization from ethanol of crude product yielded 28 ethyl 1-(6-chloropyrimidin-4-yl)-5-methyl-1H-pyrazole-4-carboxylate (B) as white crystals [47]. Yield 90%; Rf=0.8 (hexane:ethyl acetate, 4:1); m.p. 180C; 1H NMR 8.94 (s, 1H), 8.42 (s, 1H), 7.238 (s, 1H), 4.216 (q, J=7.2Hz, 2H), 2.782 (s, 3H), 1.312 (t, J=7.2Hz, 3H). EI-MS (m/z): 268.07 (M+2).

Statistics shows that 5767-35-1 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-6-hydrazinopyrimidine.

Reference:
Article; Vekariya, Mayur K.; Patel, Dhaval B.; Pandya, Pranav A.; Vekariya, Rajesh H.; Shah, Prapti U.; Rajani, Dhanji P.; Shah, Nisha K.; Journal of Molecular Structure; vol. 1175; (2019); p. 551 – 565;,
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Reference of 100707-39-9, 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.100707-39-9, name is 2-Methyl-5-bromopyrimidine-4-carboxylic acid, molecular formula is C6H5BrN2O2, molecular weight is 217.02, as common compound, the synthetic route is as follows.

A mixture of compound 5-bromo-2-methylpyrimidine-4-carboxylic acid (350 mg,1.6 mmol) in xylene (5 mL) was refluxed for 2 h. After cooling, the mixture was applied directly to a silica column, which was eluted with petroleum ether, then ethyl acetate in petroleum ether (5percent v/v) to give compound 0601-120 (170 mg, 61 >) as a white solid. LCMS: 173 [M+l]+, 1H NMR (400 MHz, DMSO-d6): delta 2.59 (s, 3H), 8.87 (s, 2H).

Statistics shows that 100707-39-9 is playing an increasingly important role. we look forward to future research findings about 2-Methyl-5-bromopyrimidine-4-carboxylic acid.

Reference:
Patent; CURIS, INC.; BAO, Rudi; LAI, Chengjung; QIAN, Changgeng; WO2011/130628; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 147972-27-8, 4-Chloro-2-(trifluoromethyl)thieno[3,2-d]pyrimidine, 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, COA of Formula: C7H2ClF3N2S, blongs to pyrimidines compound. COA of Formula: C7H2ClF3N2S

phenyl 2-trifluoromethylthieno[3,2-d]pyrimidin-4-ylmethanone (Example 1) A suspension of 4-chloro-2-trifluoromethylthieno[3,2-d]pyrimidine (0.3 g, 1.26 mmol), benzaldehyde (0.28 g, 2.64 mmol) and N,N-dimethylimidazolium iodide (0.2 g, 0.89 mmol) in THF (8 ML) was treated with NaH (60% dispersion in oil, 0.112 g, 2.8 mmol), refluxed for 15 min, cooled to room temperature, treated with water (4 ML) and the organic phase separated.. The aqueous phase was extracted with CH2Cl2 (2*20 ML), the combined organic phase washed with brine (10 ML), dried (MgSO4), concentrated in vacuo and the resulting brown oil purified by chromatography [SiO2; heptane-EtOAc (3:1)] then recrystallized from heptane to give the title compound (280 mg, 43%) as yellow needles.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,147972-27-8, 4-Chloro-2-(trifluoromethyl)thieno[3,2-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Vernalis Research Limited; US6787541; (2004); B1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 769-42-6, 1,3-Dimethylbarbituric acid, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

General procedure: A mixture of 1,3-dimethylbarbituric acid 1 (2 mmol) with an aromatic aldehyde 2a-2i (1 mmol), ammonium acetate 3 (1.2 mmol) and Fe 3 O 4 nanoparticles (0.075 g) in EtOH-H 2 O (2.5 : 2.5 mL) was refluxed for 20-35 min. The reaction was monitored by TLC. Upon completion of the process, the catalyst was separated using an external magnet. The reaction mixture was cooled down to room temperature. The crude product was filtered off and crystallized from ethanol to give compounds 5a-5f and 4g-4i in high yields. The isolated catalyst was washed with hot ethanol, dried at 60C under vacuum for 1 h and reused in the following similar experiments. The synthesized earlier products 4g-4i were characterized by IR and 1 H NMR spectra and their melting points were close to those of authentic samples [29, 30].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,769-42-6, 1,3-Dimethylbarbituric acid, and friends who are interested can also refer to it.

Reference:
Article; Fattahi; Davoodnia; Pordel; Russian Journal of General Chemistry; vol. 87; 4; (2017); p. 863 – 867;,
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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. 137281-39-1, name is 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 137281-39-1

Weigh 4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (60 g 0.2 mol) Add to a 500ml four-neck bottle,Add 200ml of DMF and 40.4g of triethylamine to the temperature to 30 C and stir to dissolve.Trityl chloride (0.3 mol) was added dropwise, the reaction was kept at 35 C for 1 hour, and DMF was evaporated to dryness under reduced pressure.Add 200ml of pure water to stir, adjust the pH to 5-6 with dilute hydrochloric acid, stir the crystal, cool down to 0-5 C, filter and dry the product.4-[2-(2-triphenylmethylamino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (molar yield) 96.3%, purity 99.1%).

The synthetic route of 137281-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lunan Pharmaceutical Group Co., Ltd.; Xia Mingjun; Zang Chao; (11 pag.)CN110305137; (2019); A;,
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Synthetic Route of 1211443-61-6, 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. 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, molecular formula is C14H17ClN4O, 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: tert-butyl (3-((4aminophenyl)sulfonamido)propyl)carbamate (4a, 560mg, 1.70mmol),2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (6,497mg, 1.70mmol),Pd(OAc)2 (30mg, 0.1equiv), BINAP (63mg, 0.06equiv), Cs2CO3(1.11g, 3.40mmol) were dissolved in 1,4-dioxane and degassed with argon for 5 min.The resulted mixture was heated to 105 C for 7 h. After monitored by TLC toobserve completion of reaction, the reaction mixture was filtered through Celite aftercooling to 25 C, then the solvents were removed in vacuo. The crude product waspurified by silica gel column chromatography to afford intermediates 7a in 42% yieldaswhite solid.

According to the analysis of related databases, 1211443-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Xin; Yu, Chenhua; Wang, Cheng; Ma, Yakun; Wang, Tianqi; Li, Yao; Huang, Zhi; Zhou, Manqian; Sun, Peiqing; Zheng, Jianyu; Yang, Shengyong; Fan, Yan; Xiang, Rong; European Journal of Medicinal Chemistry; vol. 181; (2019);,
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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. 761440-16-8, name is 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C13H13Cl2N3O2S

To a solution of 7 (200 mg, 0.979 mmol) in 0.08 M HCl inethoxyethanol (1.0 mL) and 2,5-dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine (4, 407 mg, 1.17 mmol) was added at rtand the reaction mixture was stirred at 80 C for 12 h. The solidprecipitated was filtered and washed with ethanol (2 mL). The solidfiltered was then dissolved in EtOAc (50 mL) and washed with sat.NaHCO3 (aq). The combined organic layers were concentrated underreduced pressure to obtain the crude product which was purifiedby silica gel column chromatography using MeOH/DCM (1:9)to afford the title compound (433 mg, 0.875 mmol, 94%) as a whitesolid. Mp 207.4-209.6 C; 1H NMR (300 MHz, CDCl3) delta 9.53 (s, 1H),8.53 (d, J= 8.3 Hz, 1H), 8.18 (s, 1H), 8.12 (s, 1H), 7.94 (dd, J = 7.9,1.3 Hz, 1H), 7.66 (t, J = 7.3 Hz, 1H), 7.53 (s, 1H), 7.30 (t, J = 7.9 Hz, 1H),6.83 (s, 1H), 3.90 (s, 3H), 3.26 (sept, J = 6.9 Hz, 1H), 2.45 (s, 3H), 1.79(s, 6H), 1.32 (d, J = 6.9 Hz, 6H); 13C NMR (125 MHz, CDCl3) delta 157.32,155.40, 155.33, 146.15, 138.34, 134.76, 131.36, 131.11, 128.33, 125.00,124.58, 123.55, 123.38, 122.45, 107.24, 106.48, 55.93, 55.52, 35.00,28.27, 20.78, 15.37; LC/MS m/z 513.8 [M+H+]; HRMS (EI) m/z calcdfor C25H28ClN5O3S [M+] 513.1601, found 513.1607.

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Reference:
Article; Mathi, Gangadhar Rao; Kang, Chung Hyo; Lee, Heung Kyoung; Achary, Raghavendra; Lee, Ha-Yeon; Lee, Joo-Youn; Ha, Jae Du; Ahn, Sunjoo; Park, Chi Hoon; Lee, Chong Ock; Hwang, Jong Yeon; Yun, Chang-Soo; Jung, Hee Jung; Cho, Sung Yun; Kim, Hyoung Rae; Kim, Pilho; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 536 – 549;,
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