Pyrimidines

Related Products of 330786-24-8 ,Some common heterocyclic compound, 330786-24-8, molecular formula is C17H13N5O, 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 solution of 8 (1 mmol) and substituted benzyl bromide 9 (1.2 mmol) in N, N-dimethylformamide (5 mL) was added K2CO3 (1.5 mmol) and the reaction mixture was stirred for 5 h at room temperature.The reaction solution was poured into water (50 mL). The suspension was filtered and the crude product was purified by silica gel column chromatography with dichloromethane/methanol (80/1-40/1) to give target compounds 10a – 10n.

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. 330786-24-8, 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ran, Fansheng; Liu, Yang; Liu, Meixia; Zhang, Daoguang; Wang, Peng; Dong, Junze; Tang, Wendi; Zhao, Guisen; Bioorganic Chemistry; vol. 89; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 13544-44-0, 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.13544-44-0, name is 2,4-Dichloro-5-iodopyrimidine, molecular formula is C4HCl2IN2, molecular weight is 274.88, as common compound, the synthetic route is as follows.

S-62 (20 g) was converted to S-63 by reaction S-63b and S-62 in the presence of NaHCOs in DMA at 80 C for 12h. After purification, 12 g of S-63 was obtained .

The chemical industry reduces the impact on the environment during synthesis 13544-44-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copeland; JUNG, David; (207 pag.)WO2019/136244; (2019); A1;,
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Electric Literature of 5305-40-8, 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. 5305-40-8, name is 4,6-Dichloropyrimidine-5-carbaldehyde, molecular formula is C5H2Cl2N2O, 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.

To a solution of aldehyde 14.1 (1.50 g, 8.48 mmol, 1.0 equiv.) in toluene (18 mL) was added 7 M NH3 in MeOH (1.8 mL, 12.7 mmol, 1.5 equiv.) and the reaction mixture was heated to 55 C. Additional NH3 was added (7 M in MeOH, 3.5 mL, 24.5 mmol) over the next 4 hr, and then the reaction mixture was cooled to RT. Water (2 mL) was added and the resultant mixture was concentrated. The residue was dissolve in MeOH and adsorbed onto SiO2 gel. Purification by flash column chromatography (20-25-33-40% EtOAc/hexanes) afforded 15.2 (0.88 g, 66%) as a beige solid. LCMS: m/z: 158 [M+1]+.

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 5305-40-8, 4,6-Dichloropyrimidine-5-carbaldehyde.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2009/36419; (2009); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 705263-10-1, 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. 705263-10-1, name is 6-Bromopyrazolo[1,5-a]pyrimidine, molecular formula is C6H4BrN3, 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.

6-Bromo-pyrazolo [1,5-a] pyrimidine (2.0 g, 10.0 mmol) dissolved in 20 mL of toluene, [1,1′-bis (diphenylphosphino) ferrocene Fe] dichloropalladium (0.7 g, 1 mmol), potassium acetate (4.0 g, 40.0 mmol) and the associated acid pinacol ester (5.1 g, 20.0 mmol) were added in the flask. It was heated to reflux under argon for 5 h, and TLC monitoring of the reaction process until the starting material disappeared stop heating. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography (eluent: petroleum ether / ethyl acetate). White solid, yield: 65%. 1H NMR (CDCl3, 400 MHz, delta ppm):8.71 (d, J = 1.6 Hz, 1H), 8.17 (d, J = 2.2 Hz, 1H), 1.38 (s, 12H). ESI-MS(m/z): 246.1 [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 705263-10-1, 6-Bromopyrazolo[1,5-a]pyrimidine.

Reference:
Article; Hu, Liming; Cao, Tingting; Lv, Yongjuan; Ding, Yiming; Yang, Leifu; Zhang, Qiang; Guo, Mingzhou; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5830 – 5835;,
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Synthetic Route of 155-10-2, 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. 155-10-2, name is 4-Amino-2-chloro-5-fluoropyrimidine, molecular formula is C4H3ClFN3, 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.

10287] 0.15 g (1.01 mmol) of 2-chloro-5-fluoropyrimi- dine-4-amine, 0.249 g (1.22 mmol) of (2-methyl-4,5,6,7- tetrahydrobenzothiophen-4-yl)ammonium chloride and 0.63 g (0.68 ml, 3.05 mol) of dicyclohexylethylamine in 2.0 ml of 1-methyl-2-pyrrolidone are heated at 180 C. in a closed cuvette in the microwave for 90 minutes (l3iotage Initiator, http://www.biotage.comlproduct-page/biotage-initiator).The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as mobile phase. Concentration gives 0.072 g of 5-fluoro-N2-(2-methyl-4,5,6,7-tetrahydro- 1 -benzothiophen-4-yl)pyrimidine-2,4-diamine (in waxy form) (22% yield at 85% purity).

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 155-10-2, 4-Amino-2-chloro-5-fluoropyrimidine.

Reference:
Patent; Bayer CropScience Aktiengesellschaft; JAKOBI, Harald; MINN, Klemens; BUSCATO ARSEQUELL, Estella; DIETRICH, Hansjoerg; GATZWEILER, Elmar; ROSINGER, Christopher Hugh; SCHMUTZLER, Dirk; (44 pag.)US2018/213780; (2018); A1;,
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Related Products of 13036-50-5, 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.13036-50-5, name is 2-Chloro-4-phenylpyrimidine, molecular formula is C10H7ClN2, molecular weight is 190.629, as common compound, the synthetic route is as follows.

Example 37 2-(4-(4-phenylpyrimidin-2-ylamino)phenyl)acetamidePart I: 2-(4-(4-phenylpyrimidin-2-ylamino)phenyl)acetic acidGeneral Procedure I: Microwave assisted halogen displacement with amino group [0166] A mixture of 2-chloro-4-phenylpyrimidine (0.19 g, 1.0 mmol), 2-(4- aminophenyl)acetic acid (0.38 g, 2.5 mmol), diisopropylethylamine (0.38 mL, 2.0 mmol), THF (3.0 mL) and water (1.0 mL) was placed in a seal tube and heated up to 160C in a microwave (Biotage, Model: Initiator) for 1O h. The reaction mixture was diluted with ether and washed with brine. The organic layer was separated, dried (MgSO4), and concentrated to afford 2-(4-(4-phenylpyrimidin-2-ylamino)phenyl)acetic acid in 77% yield. MS (ESI) 306 (M+H).

Statistics shows that 13036-50-5 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-4-phenylpyrimidine.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; WO2009/32861; (2009); A1;,
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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.24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, molecular formula is C6H5ClN4, molecular weight is 168.58, as common compound, the synthetic route is as follows.name: 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Adding 85 mg (about 0.5 mmol) to a 10 mL microwave reaction tube.7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, 414 mg (about 1.5 mmol) of 1-(4-(trifluoromethyl)benzyl)-1H-indole, 14 mg (about 10 mol%) of the catalyst bistrifluoromethylsulfonimide and 1 mL of the solvent HFIP, and then the microwave reaction tube was sealed.Then, the reactant in the microwave reaction tube was stirred at 100 C for 6 hours, and the solvent was distilled off under reduced pressure.And purified by column chromatography using DCM / MeOH as eluent to afford about 139 mg of pure product e16 as a white solid, yield 68%;

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Yuan Shuo; Wang Shuai; Li Zhonghua; (21 pag.)CN109180684; (2019); A;,
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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.695-86-3, name is 5-Methoxypyrimidin-4-amine, molecular formula is C5H7N3O, molecular weight is 125.13, as common compound, the synthetic route is as follows.SDS of cas: 695-86-3

General procedure: Synthesis of 2-methyl-5-((9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-yl)amino)isoindolin-1-one (4) Procedure A: A mixture of 9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-amine (3, 0.10 g, 0.37 mmol), 5-bromo-2-methylisoindolin-1-one (2, 0.10 g, 0.45 mmol), sodium tert-butoxide (54 mg, 0.56 mmol) and XPhos (5 mg, 0.01 mmol) in toluene (10 mL) was degassed with argon for 30 min. Tris(dibenzylideneacetone)dipalladium(0) (20 mg, 0.022 mmol) was added under argon atmosphere and the reaction mixture was heated at 100 C. for 12 h. After completion of the reaction, the reaction mixture was filtered through celite pad and the filtrate was concentrated. The crude residue was purified by silica gel column chromatography using 0-10% ethyl acetate in hexanes as eluent to afford 2-methyl-5-((9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-yl)amino)isoindolin-1-one (4). Yield: 0.11 g, 71%; MS (ESI) m/z 411 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,695-86-3, 5-Methoxypyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
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Synthetic Route of 13036-50-5 , The common heterocyclic compound, 13036-50-5, name is 2-Chloro-4-phenylpyrimidine, molecular formula is C10H7ClN2, 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.

Man erhitzte 0, 80 g (4, 20 MMOL) 2-CHLOR-4-PHENYLPYRIMIDIN AUS BEISPIEL 24. 1 in 3, 20 ml konz. HCI 1 Stunde auf 100 C. Anschliessend engte man den Ansatz ein, suspendierte ihn in Methylenchlorid und engte erneut ein. Ausbeute : 0, 83 g. ESI-MS : 174, 3, [M+H+] = 173, 2 ;

The synthetic route of 13036-50-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2004/80981; (2004); A1;,
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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. 444731-75-3, name is N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 444731-75-3

A 250-mL 3-necked flask equipped with a magnetic stir bar, thermometer, reflux condenser, and nitrogen inlet/outlet was charged with ethanol (60 mL, 10 volumes), the product of Intermediate Example 4 (6.00 g, 20.85 mmol, 1.0 equiv) and 5-amino-2- methylbenzenesulfonamide (4.00 g, 21.48 mmol, 1.03 equiv) with stirring. The reaction mixture was heated to 70 0C. After stirring the reaction mixture at 68 – 72 0C for 3 hrs, 4M HCI in dioxane (0.11 mL, 0.44 mmol, 0.02 equiv) was charged over ca. 2 min. The reaction mixture was stirred at 68 – 72 0C until < 1.5% by area of the starting product of Intermediate Example 4 was remaining by HPLC analysis (Typically, this reaction is complete in > 8 hrs). The reaction mixture was cooled to 20 0C over ca. 30 min and stirred at 20 – 22 0C for 40 min. The product was then isolated by filtration and the filter cake washed with ethanol (20 mL, 3.3 volumes). The wet cake was dried under vacuum at 45 – 50 0C. The monohydrochloride salt of 5-({4-[(2,3-dimethyl-2/-/-indazol- 6-yl)(methyl)amino]-pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide (9.52 g, 96.4%) was isolated as a white solid. 1H NMR (400 MHz, d6DMSO+NaHCO3) delta 9.50 (br s, 1 H), 8.55 (br s, 1 H), 7.81 (d, J = 6.2 Hz, 1 H), 7.75 (d, J = 8.7 Hz, 1 H), 7.69 (m, 1 H), 7.43 (s, 1 H), 7.23 (s, 2H), 7.15 (d, J = 8.4 Hz1 1 H), 6.86 (m, 1 H)1 5.74 (d, J = 6.1 Hz, 1 H), 4.04 (s, 3H), 3.48 (s, 3H), 2.61 (s, 3H)1 2.48 (s, 3H). MS (ES+, m/z) 438 (M+H).

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, 444731-75-3, N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/20564; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia