Category: pyrimidines

Application of 56686-16-9 ,Some common heterocyclic compound, 56686-16-9, molecular formula is C6H7BrN2O2, 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.

5-(2,4-Dimethoxypyrimidine)carboxaldehyde Prepared by the method of Example 62(b) from 5-bromo-2,4-dimethoxypyrimidine. MS (EI) 168 (M+). 1H NMR (CDCl3) 10.17 (1H, s), 8.78 (1H, s), 4.11 (3H, s), 4.09 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56686-16-9, its application will become more common.

Reference:
Patent; Baxter, Andrew; Brough, Stephen; Faull, Alan; Johnstone, Craig; McInally, Thomas; US2002/107252; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 50270-27-4, 2,4,6-Trichloropyrimidine-5-carbaldehyde, 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

A solution of 40 (6.6 g, 20 mmol) and 5-formyl-2,4,6-trichloropyrimidine (5.85 g, 27.7 mmol) in 80 ml of dry DMF was stirred at RT for 8 hr and slowly diluted with 80 ml of water. The solution produced a solid upon refrigeration for 2 days. The product was isolated by filtration, washed with cold 50percent ethanol (50 ml) and 25percent ethanol (50 ml) and dried in vacuum to yield 8.16 g (96percent) 41 as a colorless solid, mp 205-215 C. (decomp). 1H NMR (DMSO-d6) ?0.88 (t, 3H, J=7.2 Hz, CH3), 1.27 (m, 2H, CH2), 1.48 (m, 2H, CH2), 2.81-2.90 (m, 2H, CH2), 3.71-3.85 (m, 4H, CH2), 4.50 (br. s, 5H, OH, NH, H2O), 7.26 (d, 2H, J=8.4 Hz, ArH), 7.44 (d, 2H, J=8.4 Hz, ArH), 8.62 (s, 1H, 5-H).

The synthetic route of 50270-27-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epoch Biosciences, Inc.; US6699975; (2004); B2;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 862730-04-9, 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine, 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, 862730-04-9, blongs to pyrimidines compound. Product Details of 862730-04-9

Synthesis of 4-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-3-methylphenol (BA60); A solution of 4-hydroxy-2-methylphenylboronic acid (110 mg, 0.66 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (100 mg, 0.33 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by silica gel column chromatography [MeOH-CH2Cl2, 2:98] to yield BA60 (42 mg, 22% yield). ESI-MS (M+H)+ m/z calcd 284, found 284.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,862730-04-9, its application will become more common.

Reference:
Patent; Regents of the University of California; US2007/293516; (2007); 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. 1044145-59-6, name is (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H7ClN2OS

Manganese(IV) oxide, <5 micron, activated (38.1g , 439 mmol) was added to a solution of compound 223 (16.73 g, 87.8 mmol) in chloroform (800 mL). The reaction was stirred overnight, filtered through Celite, and the filtrate was concentrated in vacuo to yield compound 224 (13.7 g, 82.8% yield). 1H NMR (500 MHz, CDCl3) delta 10.31 (s, 1 H) 8.88 (s, 1 H) 2.65 (s, 2 H) ppm. 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, 1044145-59-6, (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol. Reference:
Patent; AMGEN INC.; WO2009/85185; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 57489-77-7, 5,7-Dichloropyrazolo[1,5-a]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, Application In Synthesis of 5,7-Dichloropyrazolo[1,5-a]pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 5,7-Dichloropyrazolo[1,5-a]pyrimidine

To the reaction flask, 5,7-dichloropyrazolo[1,5-a]pyrimidine (896 mg, 4.8 mmol) was added along with tert-butyl 4-aminopiperidine-1-carboxylate (954 mg, 4.8 mmol), triethylamine (664 muL, 4.8 mmol), and acetonitrile (16 mL). The reaction was heated at 100 C. for 12 hours then cooled to room temperature, diluted with water, filtered and washed with water. The product, tert-butyl 4-(5-chloropyrazolo[1,5-a]pyrimidin-7-ylamino)piperidine-1-carboxylate, was collected as a solid in quantitative yield and dried under vacuum overnight.

The synthetic route of 57489-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SENHWA BIOSCIENCES INCORPORATED; HADDACH, MUSTAPHA; TRAN, JOE A; PIERRE, FABRICE; REGAN, COLLIN F; RAFFAELE, NICHOLAS B; RAVULA, SUCHITRA; RYCKMAN, DAVID M; (482 pag.)JP5802676; (2015); B2;,
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Reference of 90349-23-8, Adding some certain compound to certain chemical reactions, such as: 90349-23-8, name is 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid,molecular formula is C9H9N3O2, 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 90349-23-8.

To a suspension of the ester compound from the procedure above (105 mg, 0.340 mmol) in DMF (0.5 mL) was added a solution of l,2-benoxazol-5-amine (46 mg, 0.340 mmol) in DMF (0.5 mL). The reaction mixture was stirred at room temperature for 2 hours until the reaction was complete, and quenched with the addition of TFA (5 drops). The precipitated solid was collected by filtration, suspended in DCM, basified with saturated aHC03to pH ~8. The aqueous layer was extracted with DCM, dried over anhydrous a2S04, filtered andconcentrated to provide a residue. The residue was purified by prep-HPLC (MeCN/H20) to provide the title compound (40 mg, 38%) as a white solid.XH NMR (400 MHz, CDC13) delta 10.31 (s, 1H), 8.72-8.71 (m, 2H), 8.45 (d, J= 1.6 Hz, 1H), 7.67 (dd, J= 9.2 Hz, 2.0 Hz, 1H), 7.60 (d, J= 9.2 Hz, 1H), 6.79 (s, 1H), 2.84 (s, 3H), 2.74 (s, 3H). ES-MS m/z: 308.0 [M+H]+. HPLC Purity (214 nm): 98%; tR= 9.36 min.

According to the analysis of related databases, 90349-23-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse, Marie Josee; (139 pag.)WO2016/73895; (2016); A1;,
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Pyrimidine – Wikipedia

Reference of 252723-16-3, 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.252723-16-3, name is 7-Benzenesulfonyl-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C13H10ClN3O2S, molecular weight is 307.76, as common compound, the synthetic route is as follows.

Step 3. To the solution of 4-chloro-6-methyl-7-(phenylsulfonyl)-7H-pyrrolo [2,3-d]pyrimidine (10 g, 32.5. mmol, 1.0 eq) in THF (400 mL), t-BuOK (18.23 g, 163.0 mmol, 5 eq) was added and stirred at RT for 12 h. Sat. NaHCO3 (50 mL) was added and extracted with EtOAc. The organic layers were separated, dried and concentrated to afford 4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine as a brown solid (2.7 g, 50 % in yield).

Statistics shows that 252723-16-3 is playing an increasingly important role. we look forward to future research findings about 7-Benzenesulfonyl-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; BABLER, Martin; GERRITSEN, Mary E.; WO2014/22569; (2014); A1;,
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Pyrimidine – Wikipedia

Related Products of 93366-88-2, Adding some certain compound to certain chemical reactions, such as: 93366-88-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-2-amine,molecular formula is C6H6N4, 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 93366-88-2.

7H-pyrrolo[2,3-d]pyrimidin-2-amine (134 mg, 1.00 mmol), QC130 (381 mg, 1.29 mmol), potassium carbonate(415 mg, 3.00 mmol) and valine (23 mg, 0.2 mmol) It was added to an eggplant type flask, dimethyl sulfoxide wasadded, and the reaction solution was deoxidized. Copper iodide (19 mg, 0.1 mmol) was added and the reactionsolution was deoxygenated. Heat to 90C and stir for 16 hours. After the reaction was completed, it was cooledto room temperature, water and ethyl acetate were added, and the mixture was filtered over Celite. The targetcompound was obtained in an amount of 110 mg.

According to the analysis of related databases, 93366-88-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Zhiqiang; Yan Ziqin; Li Jia; Zhou Yubo; Su Mingbo; Chen Zheng; (138 pag.)CN109810110; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
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Adding a certain compound to certain chemical reactions, such as: 514854-13-8, 6-Ethyl-5-iodopyrimidine-2,4-diamine, 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, 514854-13-8, blongs to pyrimidines compound. SDS of cas: 514854-13-8

According to general Sonogashira coupling procedure ethyl-iodopyrimidine (0.065 g, 0.25 mmol), CuI (0.009g, 0.049 mmol, 20mol%), Pd(PPh3)2Cl2 (0.017 g, 0.025mmol, 10mol%) and alkyne 17 (0.110 g, 0.374 mmol) were reacted in DMF/Et3N ( 1ml each) at 65C for 12 hrs. After the mixture was cooled, the dark brown solution was concentrated and the product was purified by flash chromatography (SiO2 10 g, 2% MeOH/CHC2) followed by reverse phase flash chromatography (NH2 capped SiO2, CHCl2) to afford coupled pyrimidine 19 as a pale solid (0.085 g, 80%). 1H NMR (500 MHz, CDCl3) delta 7.17 (s, 1H), 7.11 (d, J = 2.15 Hz, 1H), 7.07 (dd, J = 2.19, 8.34 Hz, 1H), 6.97 – 6.93 (m, 2H), 6.92 (d, J = 8.36 Hz, 1H), 5.19 (s, 2H), 4.96 (s, 2H), 4.29 (s, 4H), 4.05 (q, J = 7.06 Hz, 1H), 3.85 (s, 3H), 2.71 (q, J = 7.55 Hz, 2H), 1.61 d, J = 7.1Hz, 3H), 1.24 (t, J = 7.57 Hz, 3H); 13C NMR (125 MHz, CDCl3) delta 173.27, 164.26, 160.61, 160.16, 145.23, 143.63, 143.33, 142.40, 134.53, 120.15, 117.89, 117.52, 115.89, 111.15, 110.64, 101.55, 90.57, 75.40, 64.45, 64.41, 55.34, 33.14, 29.65, 24.71, 12.54; HRMS (DART, MH+) m/z 431.2093 (calculated for C25H27N4O3, 431.2083).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,514854-13-8, its application will become more common.

Reference:
Article; Paulsen, Janet L.; Viswanathan, Kishore; Wright, Dennis L.; Anderson, Amy C.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1279 – 1284;,
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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.31462-54-1, name is 2-Iodopyrimidine, molecular formula is C4H3IN2, molecular weight is 205.98, as common compound, the synthetic route is as follows.Computed Properties of C4H3IN2

Example 28 General Procedure for the Palladium-Catalyzed Cross-Coupling of ArylIodides with l -Trityl-lH-imidazol-4-yl)zinc(II) chloride; ,[0349] To a stirred solution of 4-iodo-1-trityl-lH-imidazole (218.0 mg, 0.5 mmol) in anhydrous THF (4 mL) at room temperature was added EtMgBr (1.0 M in THF, 0.5 mmol, 0.5 mL) dropwise, under an atmosphere of N2. The resulting solution was allowed to stir for 90 min and anhydrous ZnCl2 (0.5 mmol, 68.2 mg) was added. The resulting white suspension was allowed to stir for 90 min and a solution of the aryl iodide (0.5 mmol) in THF (1 mL) was added followed by the immediate addition of Pd(PPlV}) (56 mg, 0.05 mmol). The reaction mixture was allowed to stir at 70 C for 12 h under an atmosphere of N2. After cooling to room temperature, the solution was diluted with CH2C12 (10 mL) and the organic layer was washed with an EDTA (aq) buffer (pH = 9) (2 x 5 mL) and brine. The organic layer was dried (Na2SC>4) and concentrated under reduced pressure. The crude residue was used in next step without further purification. To a solution of the crude imidazole from the previous step was added trifluoroacetic acid (1.0 mL) and MeOH (4.0 mL). The solution was stirred at 80 C for 2 h. The reaction mixture was allowed to cool to room temperature and the pH was adjusted to -10 with 10% NaOH (aq). The aqueous phase was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with water, brine, and dried. The solvent was removed in vacuo to afford the crude residue, which was purified by flash column chromatography on silica gel to afford the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,31462-54-1, 2-Iodopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NEWLINK GENETICS; MAUTINO, Mario, R.; KUMAR, Sanjeev; JAIPURI, Firoz; WALDO, Jesse; KESHARWANI, Tanay; ZHANG, Xiaoxia; WO2011/56652; (2011); A1;,
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