Pyrimidines

Application of 252723-17-4, 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 252723-17-4, name is 5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 7-Benzenesulfonyl-5-bromo-4-chloro-7H-pyrrolo [2,3- d] pyrimidine (4.9 g, 13 mmol), Piperazine-l-carboxylic acid tert-butyl ester (3.7g, 20 mmol), and DIPEA (5.7 mL, 33 mmol) in IPA (30 mL) was stirred and heated at reflux for 6 hours. The mixture was cooled to-10 C, the solids collected by vacuum filtration, rinsed with cold IPA and dried under vacuum to give 4- (7-Benzenesulfonyl-5-bromo-7H-pyrrolo [2,3- d] pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (5.9g, 86%. ) LCMS (APCI+) m/z 522 and 524 [M+H] + ; Rt: 3.92 min. 1H NMR (DMSO-d6,400 MHz) 5 8. 48 (1H, s), 8.21 (2H, d, J 8. 2 Hz), 7.66-7. 62 (2H, m), 7.54 (2H, t, J 7. 8 Hz), 3.62-3. 55 (8H, m), 1. 48 (9H, s.)

According to the analysis of related databases, 252723-17-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2005/51304; (2005); A2;,
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Electric Literature of 14080-59-2, 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.14080-59-2, name is 4-Chlorothieno[2,3-d]pyrimidine, molecular formula is C6H3ClN2S, molecular weight is 170.62, as common compound, the synthetic route is as follows.

Examples 308 and 309 Synthesis of 6-bromo-4-chlorothieno[2,3-d]pyrimidine and 6-bromo-2-butyl-4-chlorothieno[2,3-d]pyrimidine n-BuLi (1.6 M in hexane, 1.9 ml, 2.5 mmol) in THF (8 ml) was cooled to -78 C. 4-Chlorothieno[2,3-d]pyrimidine (0.34 g, 2.0 mmol) was dissolved in THF (2 ml) and slowly added to the reaction mixture over 5 minutes. After 20 min, CBr4 (0.73 g, 2.2 mmol) in THF (3 ml) was slowly added to the reaction mixture. The temperature was maintained at -78 C. for 20 minutes and then warmed to room temperature for 2 hours. The mixture was poured into water and extracted with chloroform, dried over sodium sulfate, and concentrated in vacuo. The crude residue was purified by silica gel chromatography (EtOAc/hexane 40:1) to yield two pure compounds a white solid (example 203: 0.13 g, 25% and example 204: 0.16 g, 26%).

The chemical industry reduces the impact on the environment during synthesis 14080-59-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Katholieke Universiteit Leuven, K.U. Leuven R&D; Herman, Jean; Louat, Thierry; US2014/88088; (2014); A1;,
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Electric Literature of 145783-15-9 ,Some common heterocyclic compound, 145783-15-9, molecular formula is C7H9Cl2N3S, 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.

A mixture of (1S,2S,3R,5S)-3-amino-5-(2-hydroxyethoxy)cyclopentane-1,2-diol (OLA; 1.06 g, 6 mmol), 4,6-dichloro-2-(propylthio)pyrimidin-5-amine (CLINA; 1.43 g, 6 mmol), triethylamine (1.09 g, 7.8 mmol) and polyethyleneglycol PEG400 (2 mL) was stirred for 48 h at 75 C. The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (25 mL) and evaporated under reduced pressure to give a resinous material which solidified upon trituration in n-hexane (25 mL). After filtration there was obtained OLACINA as a grey powder (2.0 g, 88% yield): 13C NMR (DMSO-d 6, 125 MHz) delta 13.3, 22.8, 32.2, 34.7, 54.8, 60.4, 69.8, 72.4, 75.2, 82.4, 119.9, 137.5, 152.5, 155.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,145783-15-9, its application will become more common.

Reference:
Patent; LEK Pharmaceuticals d.d.; The designation of the inventor has not yet been filed; EP2607355; (2013); A1;,
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Reference of 514854-13-8, 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.514854-13-8, name is 6-Ethyl-5-iodopyrimidine-2,4-diamine, molecular formula is C6H9IN4, molecular weight is 264.07, as common compound, the synthetic route is as follows.

According to a general Sonogahisra coupling procedure, ethyl-iodopyrimidine (0.105 g, 0.4 mmol), CuI (0.028 g, 0.08 mmol, 21 mol %), Pd(PPh3)2Cl2 (0.028 g, 0.04 mmol, 10 mol %) and alkyne 45 (0.123 g, 0.6 mmol) were reacted in DMF/Et3N (1.3 mL each) at 60 C. for 12 h. After the mixture was cooled, dark reddish brown solution was concentrated and the product was purified by flash chromatography (SiO2, 5 g, 2% MeOH/CHCl3) to afford coupled pyrimidine 48 as a pale white powder (0.099 g, 71%) followed by reverse phase flash chromatography (NH2 capped SiO2, 3 g, 100% CH2Cl2, 1% MeOH/CH2Cl2) for biological evaluation: TLC Rf=0.1 (5% MeOH/CH2Cl2); mp 161.3-162.8 C.; 1H NMR (500 MHz, CDCl3) delta 8.84 (s, 2H), 8.62-8.02 (m, 2H), 7.88-7.37 (m, 3H), 5.16 (s, 2H), 4.98 (s, 2H), 4.10 (q, J=7.1 Hz, 1H), 2.67 (q, J=7.6 Hz, 2H), 1.65 (d, J=7.2 Hz, 3H), 1.22 (t, J=7.6 Hz, 3H); 13C NMR (12 MHz, CDCl3) delta 174.1, 164.4, 163.8, 161.1, 156.1, 137.5, 133.9, 130.9, 128.8, 128.3, 99.2, 89.9, 29.9, 28.7, 24.3, 12.7; IR (neat cm-1) 3401, 3312, 3159, 2970, 2933, 2871, 2222, 1623, 1563, 1427, 802, 740, 687; HRMS (ESI, M++H) m/z 345.1817 (calculated for C20H21N6, 345.1822); HPLC (a) tR=6.7 mins, 99.6%, (b) tR=7.6 mins, 99.6%

The chemical industry reduces the impact on the environment during synthesis 514854-13-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wright, Dennis L.; Anderson, Amy C.; Sormunen, Grant; US2015/225353; (2015); A1;,
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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. 95928-49-7, name is Ethyl 2-hydroxypyrimidine-5-carboxylate, the common compound, a new synthetic route is introduced below. Safety of Ethyl 2-hydroxypyrimidine-5-carboxylate

Step 10d: Ethyl 2-chloropyrimidine-5-carboxylate (Compound 0305)[0216]A mixture of compound 0304 (3.60 g, 21 mmol), phosphorus oxychloride (25 mL), and N,N-dimethylaniline (2.5 mL) was heated at reflux for 1.5 h. After removal of the solvent, ice water (10 mL) was added to the residue. The mixture was added to 2 N NaOH (90 ml), and extracted with EtOAc. The organic layer was evaporated and purified by column chromatography (ethyl acetate in petroleum ether, 5percent v/v) to give compound 0305 (1.20 g, 30percent): LCMS: 187 [M+1]+, 1H NMR (300 MHz, CDCl3): delta 1.42 (t, J=7.5 Hz, 3H), 4.48 (q, J=7.5 Hz, 2H), 9.15 (s, 2H); 1H NMR (400 MHz, DMSO-d6): delta 1.33 (t, J=6.8 Hz, 3H); 4.37 (q, J=6.8 Hz, 2H), 9.18 (s, 2H).

The synthetic route of 95928-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Curis, Inc.; Bao, Rudi; Lai, Chengjung; Qian, Changgeng; US2013/102595; (2013); A1;,
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Related Products of 696-82-2 ,Some common heterocyclic compound, 696-82-2, molecular formula is C4HF3N2, 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.

(1) 1-Acetyl-4-(4,6-difluoropyrimidin-2-yl)piperazine To a solution of 2,4,6-trifluoropyrimidine (2.0 g) and potassium carbonate (3.1 g) in acetonitrile (15 ml) was added a solution of 1-acetylpiperazine (1.9 g) in acetonitrile (5 ml) over 10 min under ice-cooling and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a pale-yellow oil. The obtained pale-yellow oil was purified by silica gel column chromatography to give the title compound (1.8 g) and 1-acetyl-4-(2,6-difluoropyrimidin-4-yl)piperazine (1.7 g) both as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,696-82-2, its application will become more common.

Reference:
Patent; Mitsubishi Pharma Corporation; US6455528; (2002); B1;,
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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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. A new synthetic method of this compound is introduced below., Product Details of 22536-66-9

2.4. 2-[1-[2-(4-Fluorophenoxy)ethyl]piperidin-4-ylamino]-pyrimidine-4-carboxamide, hydrochloride. 5.5 g (0.02 mol) of 1-[2-(4-fluorophenoxy)ethyl]-piperidin-4-amine, 3.15 g (0.02 mol) of 2-chloropyrimidine-4-carboxamide, 6.91 g (0.05 mol) of potassium carbonate and 0.4 g of sodium iodide are suspended, under argon, in 40 ml of N,N-dimethylformamide. The mixture is stirred at room temperature for 17 hours and then at 40-45 C. for 8 hours. The mixture is cooled to room temperature, poured into 150 ml of water and extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. After chromatography on silica (eluent: dichloromethane/methanol 97.5/2.5 to 90/10), 4.95 g of base are obtained. The hydrochloride is prepared from it by reaction with a 0.1N hydrochloric acid solution in 2-propanol. After recrystallisation from ethanol, 4.1 g of compound are obtained. Melting point: 202-205 C.

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, 22536-66-9, 2-Chloropyrimidine-4-carboxamide.

Reference:
Patent; Synthelabo; US5246939; (1993); A;,
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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. 2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine. A new synthetic method of this compound is introduced below., Safety of 2,4-Dichloro-5-fluoropyrimidine

To a solution of 2,4-dichloro-5-fluoropyrimidine (1 .02 g, 6.08 mmol) inTHF/NMP (38 mL/3 ml_) was added Fe(acac)3 (215 mg, 0.61 mmol) and the mixture was cooled to 0 oC. 3.0 M methylmagnesium bromide in Et2O (3.04 ml_, 9.12 mmol) was added dropwise. After 30 min at 0 oC, the reaction was complete and quenched with saturated aqueous NH CI solution. Et2O was added and the layers were separated and the aqueous layer was further extracted with several portions of Et2O. The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (Hexanes to 10% EtOAc/Hexanes) gave the desired product as a waxy white solid (430 mg, 48%). 1H NMR (400 MHz, CDCI3): 8.35 (s, 1 H), 2.55 (d, J = 2.5 Hz, 3H).

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, 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHAI, Wenying; LETAVIC, Michael, A.; LY, Kiev, S.; PIPPEL, Daniel, J.; RUDOLPH, Dale, A.; SAPPEY, Kathleen, C.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; SOYODE-JOHNSON, Akinola; STOCKING, Emily, M.; SWANSON, Devin, M.; WO2011/50198; (2011); A1;,
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Synthetic Route of 289042-12-2 , The common heterocyclic compound, 289042-12-2, name is tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate, molecular formula is C29H40FN3O6S, 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 4 (3R,5S,6E)-7-[4-(4-Fluorophenyl)-2-[Methyl(Methylsulfonyl)Amino]-6-(Propan-2-Yl)Pyrimidin-5-Yl]-3,5-Dihydroxyhept-6-Enoic Acid-2-Methylpropan-2-Amine (1:1) Hydrochloric acid (2 N; 60 mL) was added to a solution of tert-butyl [(4R,65)-6-{(E)-2-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]ethenyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate (Example 3; 50 g) in acetonitrile (500 mL) at room temperature and stirred at the same temperature for 3 hours. After completion of the reaction, aqueous solution of sodium hydroxide (10%; 90 mL) was added to the reaction mixture at room temperature and the temperature of the mixture was allowed to rise to 40 C. to 45 C. The pH of the reaction mixture was adjusted to 12 to 12.8 using aqueous solution of sodium hydroxide (10%). Acetonitrile was recovered completely under vacuum at 45 C. to 50 C. De-ionized water (250 mL) was added to the resulting residue at room temperature. Methyl tert-butyl ether (200 mL) was added to the mixture and stirred for 10 minutes. Layers were separated and methyl tert-butyl ether (200 mL) was added to the aqueous layer and stirred for 10 minutes. Layers were separated and aqueous layer was cooled to 5 C. to 10 C. and adjusted to a pH of 3.5 to 4.0 using hydrochloric acid (2N). Dichloromethane was added to the resulting mixture and stirred for 10 minutes to 15 minutes. Dichloromethane was recovered completely under vacuum at 35 C. to 40 C. Acetonitrile (500 mL) was added to the resulting residue and mixture was cooled to 0 C. to 5 C. To this cooled layer, tert-butyl amine (7 g) was slowly added for 30 minutes at 0 C. to 5 C. and stirred for 2 hours at 10 C. to 15 C. The product was filtered, washed with acetonitrile (50 mL) and dried under vacuum at 45 C. for 3 hours. Dry weight: 40 g

The synthetic route of 289042-12-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; Pandya, Vishwesh Pravinchandra; Richhariya, Santosh; Divya, Prabhakar; Meeran, Hashim Nizar Poovanathil Nagoor; Tewari, Neera; US2013/150579; (2013); A1;,
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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 24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H5ClN4

General procedure: A mixture of 4 (50 mg; 0.296 mmol), Na2CO3 (60.74 mg; 0.592 mmol), Pd(PPh3)4 (34.66 mg; 0.030 mmol) and boronic acid (1.5 equiv.) was heated at 130 C in dioxane/water (4/1, 3 mL) for 3h. The reaction was followed by TLC. After completion, the mixture was filtered by celite and concentrated under vacuum. The solid obtained was submitted to a column chromatography. The increase of polarity in solvent gradient was made from neat petroleum ether to mixture of AcOEt/petroleum ether (6:4).

With the rapid development of chemical substances, we look forward to future research findings about 24415-66-5.

Reference:
Article; Loubidi, Mohammed; Moutardier, Anais; Campos, Joana F.; Berteina-Raboin, Sabine; Tetrahedron Letters; vol. 59; 11; (2018); p. 1050 – 1054;,
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