Month: March 2022

Application of 69696-37-3 , The common heterocyclic compound, 69696-37-3, name is 5-Bromo-2,4-dimethylpyrimidine, molecular formula is C6H7BrN2, 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 60 -((3-carbamoyl-7-(2,4-dimethylpyrimidin-5-yl)-8-fluoroquinolin-4-yl)amino)-5- cyclopentylbenzoic acid a) methyl 3-((3-carbamoyl-7-(2,4-dimethylpyrimidin-5-yl)-8-fluoro 5-cyclopentylbenzoate. A mixture of methyl 3-((7-bromo-3-carbamoyl-8- fluoroquinolin-4-yl)amino)-5-cyclopentylbenzoate (220 mg, 0.452 mmol), bis(pinacolato)diboron (132 mg, 0.520 mmol), potassium acetate (155 mg, 1 .583 mmol), [1 , 1 ‘-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) dichloromethane adduct (18.47 mg, 0.023 mmol) and 1 ,4-dioxane (3 mL) was purged with nitrogen for 15 minutes, then heated at 1 10 C for 30 minutes in a microwave reactor. 5-Bromo-2,4-dimethylpyrimidine (67.7 mg, 0.362 mmol), cesium carbonate (368 mg, 1.131 mmol), [1 , 1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium(ll) dichloromethane adduct (18.47 mg, 0.023 mmol) and water (1 mL) were added. The mixture was purged again with nitrogen for 15 minutes, then heated in a microwave reactor at 1 10 C for 30 min. After cooling, the mixture was filtered and then partitioned between ethyl acetate and brine. The combined organics were dried (Na2S04), filtered, and concentrated to a brown residue. This residue was purified on silica gel (0-10% 2- propanol/ethyl acetate, then 10-30% 2-propanol/ethyl acetate) to afford a yellow solid. The solid was further purified by reverse-phase preparative HPLC (ODS, acetonitrile/0.03% aqueous ammonia) to afford the title compound (135 mg, 58%) as a yellow solid. LCMS (ES+) m/e 514 [M+H]+.

The synthetic route of 69696-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROWN, Kristin, K.; CHAI, Deping; DODSON, Christopher, S.; DUFFY, Kevin, J.; SHAW, Antony, Nicholas; WO2013/96151; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 99420-75-4, 5-Methylpyrimidine-2-carboxylic 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

To a solution of 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24 mmol) in DMF(72.4 mL) was added 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24mmol), and N,Odimethylhydroxylaminehydrochloride (0.777 g, 7.96 mmol). The mixture was cooled to0 C and 1-propanephosphonic acid cyclic anhydride, 50 wt.% solution in EtOAc (9.21mL, 14.48 mmol) was added dropwise. The mixture was allowed to warm toRTovernight. LCMS indicated complete conversion to product. The mixture was dilutedwith water, extracted with CHCb:IPA (3:1) and washed with brine and NaHC03. Themixture was then dried over Na2S04, concentrated in vacuo and purified by silica gelchromatography (0-100% heptanes:EtOAc) to yield Example 209.11 (0.7 g, 3.86 mmol,53.4% yield). 1H NMR (500 MHz, CDCb) o 8.61- 8.69 (m, 2 H) 3.61 -3.79 (m, 3 H)3.27- 3.47 (m, 3 H) 2.34- 2.45 (m, 3 H). LCMS-ESI (pos) m/z: 182.2 (M+Ht.

The synthetic route of 99420-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; (434 pag.)WO2018/93577; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1333240-17-7 ,Some common heterocyclic compound, 1333240-17-7, molecular formula is C6H7ClN2O2, 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.

b. Preparation of Compound 2-(4-Fluorophenyl)-4,5-dimethoxypyrimidine 2-Chloro-4,5-dimethoxypyrimidine (500 mg, 2.86 mmol), (4-fluorophenyl)boronic acid (601 mg, 4.30 mmol), Pd(PPh3)4 (330 mg, 0.29 mmol) and Na2CO3(910 mg, 8.59 mmol) were dissolved in a mixture of dioxane (12 mL) and water (4 niL). The air was evacuated and replaced with N2. Then, the reaction mixture was refluxed for 5 hours. After the reaction was completed, it was cooled to room temperature and it was diluted with EtOAc and washed with sat. NH4CI followed by brine. The organic layer was dried over Na2S04 and concentrated under reduced pressure and the resulting residue was flash chromatographed on silica gel eluting with 0 to 10% EtOAc/Hexane. This afforded 2-(4-fluorophenyl)-4,5-dimethoxypyrimidine as a white solid (123 mg, 77%); m.p.l 14-116 C; LH NMR (400 MHz, CDC13) delta 8.37 (dd, J= 9 Hz, J= 6 Hz, 2H), 8.12 (s, 1H), 7.16 – 7. 12 (m, 2H), 4.17 (s, 3H), 3.98 (s, 3H); 13C NMR (100 MHz, CDCI3) delta 163.1 (JQF= 248 Hz), 159.7, 155.3, 141.0, 137.2, 133.6 (JCIF= 3 Hz), 129.6 (J F= 8 Hz), 115.3 (JC,F= 22 Hz), 56.4, 54.0; 19F NMR (376 MHz, CDC13) delta -11 1.9.

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. 1333240-17-7, 2-Chloro-4,5-dimethoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LAVOIE, Edmond J.; BAUMAN, Joseph David; PARHI, Ajit; SAGONG, Hye Yeon; PATEL, Disha; ARNOLD, Eddy; DAS, Kalyan; VIJAYAN, Suyambu Kesava; WO2014/43252; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 43024-61-9 ,Some common heterocyclic compound, 43024-61-9, molecular formula is C9H9N3O3, 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.

Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate (Journal of Medicinal Chemistry, vol. 49, page 2526, 2006) (3.20 g, 15.5 mmol) was dissolved in phosphorus oxychloride (30 mL), N,N-diisopropylethylamine (5.4 mL, 30.9 mmol) was added, and the mixture was stirred with heating at 100 C. for 3 hr. After confirmation of consumption the starting materials, phosphorus oxychloride was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was added dropwise to a saturated aqueous sodium hydrogen carbonate solution under ice-cooling. To the saturated aqueous sodium hydrogen carbonate solution was added ethyl acetate, and the mixture was extracted 3 times. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.

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. 43024-61-9, Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYOWA HAKKO KIRIN CO., LTD.; Yamamoto, Keisuke; Aratake, Seiji; Hemmi, Kazuki; Mizutani, Mirai; Seno, Yuko; US2014/221340; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1123-95-1, 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 1123-95-1, name is 5-Hydroxymethylcytosine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 6; A reaction solution (1.0 mL) containing 2′-deoxyribose 1-phosphate di(monocyclohexylammonium) salt (50 mM, SIGMA), 5-hydroxymethylcytosine (10 mM, SIGMA), a sodium acetate buffer (pH 8.0, 100 mM), and the enzyme solution (0.1 mL) prepared in Reference Example 2 was heated at 50 C. for one hour to perform the enzymatic reaction. The reaction solution was diluted for analysis. According to the analysis, a corresponding nucleoside compound was generated (0.1 mM).

According to the analysis of related databases, 1123-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsui Chemicals, Inc.; US2005/74857; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 53557-69-0, 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.53557-69-0, name is 6-Iodopyrimidin-4-amine, molecular formula is C4H4IN3, molecular weight is 221, as common compound, the synthetic route is as follows.

Step 9: 4-(6-Aminopyrimidin-4-yl)-1-(5-chloro-2-methylphenyl)-1 H-pyrrole-2-carbonitrilento a 50 mL round bottom flask equpped wfth a stir bar, condenser and 3-way vave connected to argon and vacuum 1 -(5-chloro-2-methylphenyl)-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrole-2-carbonitrile coming from the previous step, 6-iodopyrimidin-4-amine (663 mg, 3.0 mmol), 2M Na2003 (3.0 mL, 6.0 mmol) and dioxane (20 mL) were charged at room temperature. The resuWng reacton mixture was degassed three times back fAhng wfthfour times back flWng wfth argon each time and then warmed to 110 C for 1 h. The reacton mixture was coo?ed to room temperature, fUtered through a pad of Cehte, washed wfth EtOAc, and the fUtrate was concentrated and then dUuted wfth EtOAc and water. The two ayers were separated, and the aqueous ayer was extracted wfth EtOAc, The combned organic fractions were washed wfth aqueous brne, dried over Na2SO4, fNtered and concentrated under reduced pressure. The residue was purified by Biotage SP1 Elash Chromatography (DCM/MeOH/7N NH3 n MeOH95/5/05) to afford the tfte compound (291 mg, 47%, 2 steps).1H NMR (400 MHz, DMSO-d6) 8.33 (d, J = 0.98 Hz, 1 H), 7.96 (d, J = 1.7 Hz, 1 H), 7.64 – 7.69 (m, 2H), 7.55 – 7.61(m, 1H), 7.50-7.54 (m, 1H), 6.81 (s, 2H), 6.65 (d, J = 1.1 Hz, 1H), 2.10 (s, 3H).HRMS (ESI) m/z calcd for C16H12C1N5 + H 310.0854, found 310.0858.

Statistics shows that 53557-69-0 is playing an increasingly important role. we look forward to future research findings about 6-Iodopyrimidin-4-amine.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria Gabriella; BINDI, Simona; CALDARELLI, Marina; NESI, Marcella; ORRENIUS, Sten Christian; PANZERI, Achille; WO2014/19908; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 52854-14-5, 4-Chloro-6-methoxy-5-nitropyrimidine, 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, Recommanded Product: 4-Chloro-6-methoxy-5-nitropyrimidine, blongs to pyrimidines compound. Recommanded Product: 4-Chloro-6-methoxy-5-nitropyrimidine

b) 4-Methoxypyrimidin-5-amine 10% Palladium on carbon (1.10 g) was added to a solution of 4-chloro-6-methoxy-5-nitropyrimidine (Preparation 25a, 1.97 g, 10.4 mmol) in ethanol (80 mL) and the reaction mixture was stirred at ambient temperature overnight under a hydrogen atmosphere at a pressure of 2 bars. The mixture was then filtered through Celite and the filter cake was washed with ethanol. The combined filtrate and washings were concentrated to give the title compound (1.30 g, 100%) as a solid. LRMS (m/z): 126 (M+1)+. 1H NMR delta (300 MHz, DMSO-d6): 4.11 (s, 3H), 7.91 (s, 1 H), 8.59 (s, 1 H).

The synthetic route of 52854-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Almirall, S.A.; EP2527344; (2012); A1;,
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. 16462-29-6, name is 4-Amino-2-(ethylthio)-5-pyrimidinecarbonitrile, molecular formula is C7H8N4S, 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. Recommanded Product: 4-Amino-2-(ethylthio)-5-pyrimidinecarbonitrile

4-Amino-2-ethylthiopyrimidine-5-carboxamide. 4-Amino-5-cyano-2-ethylthiopyrimidine (4.0 g, 22.3 mmol) is added to sulfuric acid (conc., 4.3 mL) in small portions. The mixture is then stirred under N2 at 40 C. for 1.5 h. The reaction is quenched with ice-water and NH4 OH is used to adjust the pH to ~9. The solid is collected via suction filtration and dried in a vacuum oven overnight. 4-Amino-2-ethylthiopyrimidine-5-carboxamide (2.58 g, 58%) is obtained as a light brown solid. 1 H NMR: (DMSO) delta 8.52 (1H, s), 7.98 (2H, brs), 7.42 (2H, brs), 3.04 (2H, q, J=7.3 Hz), 1.27 (3H, t, J=7.3 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 16462-29-6.

Reference:
Patent; Warner-Lambert Company; US5654307; (1997); A;,
Pyrimidine | C4H4N2 – PubChem,
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. 6939-11-3, name is 5-Methoxy-2-thioxo-2,3-dihydropyrimidin-4(1H)-one. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6939-11-3

Intermediate 17; 5-(Methoxy)-2,4(1H,3H)-pyrimidinedione A mixture of 5-(methoxy)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (21.5 g; 0.137 moles), chloroacetic acid (21.5 g; 0.227 moles), and water (585 mL) was refluxed for 2 h. Concentrated HCl (85 mL) was added and the mixture was then refluxed for 16 h. Upon cooling, a solid formed and was collected by filtration, washed with water and dried to yield the desired product (18.2 g; 94% yield). MS: (M+H)+=143.

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, 6939-11-3, 5-Methoxy-2-thioxo-2,3-dihydropyrimidin-4(1H)-one.

Reference:
Patent; Johnson, Neil W.; Bryan, Deborah L.; US2008/182852; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1060815-90-8, 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.1060815-90-8, name is 2-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3ClIN3, molecular weight is 279.47, as common compound, the synthetic route is as follows.

Methyl 2-bromo-2-methylpropanoate (663 mL, 5.13 mmol) was added to 2-chloro-5- iodo-7H-pyrrolo[2,3-c/]pyrimidine (Preparation 74, 358.1 g, 1 .28 mol), potassium iodide (21 .3 g, 128 mmol) and cesium carbonate (1670 g, 5.13 mol) in DMF (7162 mL). The mixture was heated at 60C for 19 hours. The reaction mixture was diluted with water (7000 mL) and stirred at room temperature for 42 hours. The mixture was filtered and the solid was washed with water (500 mL) to afford the title compound as a beige solid in 92% yield, 445.8 g. 1H NMR (400 MHz, CDCl3): delta ppm 1.89 (s, 6H), 3.65 (s, 3H), 7.39 (s, 1 H), 8.56 (s, 1 H)

Statistics shows that 1060815-90-8 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; PFIZER LIMITED; ANDREWS, Mark, David; BAGAL, Sharanjeet, Kaur; BROWN, David, Graham; GIBSON, Karl, Richard; OMOTO, Kiyoyuki; RYCKMANS, Thomas; SABNIS, Yogesh; SKERRATT, Sarah, Elizabeth; STUPPLE, Paul, Anthony; WO2014/53967; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia