Category: pyrimidines

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.60186-89-2, name is 4-Bromo-2,6-dimethoxypyrimidine, molecular formula is C6H7BrN2O2, molecular weight is 219.036, as common compound, the synthetic route is as follows.Recommanded Product: 60186-89-2

To a microwave vial was charged (R) -5- (1-hydroxy-2- (2, 8-diazaspiro [4.5] decan-8-yl) ethyl) -4-methylisobenzofuran-1 (3H) -one (40 mg, 0.121 mmol) , 4-bromo-2, 6-dimethoxypyrimidine (26.5 mg, 0.121 mmol) , tris (dibenzylideneacetone) dipalladium (0) (5.54 mg, 6.05 mumol) , 2-dicyclohexylphosphino-2?, 4?, 6?-triisopropylbiphenyl (11.5 mg, 0.024 mmol) , and potassium phosphate (51.4 mg, 0.242 mmol) . The vial was sealed, degased, and filled with dioxane (0.60 mL) . The reaction mixture was heated at 100 overnight, diluted with water, extracted with EtOAc. The organic layer was washed with brined, dried, evaporated to give the crude product, which was purified by silica gel column chromatography (0-10 MeOH/DCM) to afford (R) -5- (2- (2- (2, 6-dimethoxypyrimidin-4-yl) -2, 8-diazaspiro [4.5] decan-8-yl) -1-hydroxyethyl) -4-methylisobenzofuran-1 (3H) -one. LC-MS (ESI, m/z) : 469 [M+1] +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60186-89-2, 4-Bromo-2,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; JIANG, Jinlong; SHI, Zhi-Cai; WALSH, Shawn P.; WU, Zhicai; YU, Yang; FERGUSON II, Ronald; GUO, Zhiqiang; FRIE, Jessica; SUZUKI, Takao; BLIZZARD, Timothy A.; FU, Qinghong; VANGELDER, Kelsey F.; (118 pag.)WO2016/65582; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 29458-38-6, 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.29458-38-6, name is 6-Methoxypyrimidine-2,4(1H,3H)-dione, molecular formula is C5H6N2O3, molecular weight is 142.11, as common compound, the synthetic route is as follows.

A mixture of 2,4-dihydroxy-6-methoxypyrimidine (15g, 0.106mol) in phosphorus (III) oxychloride (400ml) was heated under reflux for 4 hours to give a solution. Excess phosphorus (III) oxychloride was removed by evaporation, the residue treated with ice/water and extracted with EtOAc. The combined extracts were washed with water, dried (Na2SO4) and the solvent removed by evaporation to give 2,4-dichloro-6-methoxypyrimidine as an oil (5.5g, 30%); NMR.3.96 (3H, s), 6.63 (IH, s); m/z_179 [MH]+.

Statistics shows that 29458-38-6 is playing an increasingly important role. we look forward to future research findings about 6-Methoxypyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/31745; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 923282-39-7, 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. 923282-39-7, name is 7-Chloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

Example 4: Preparation of N-[2-[3-methoxy-4-[[2-(trifluoromethyl)-4-pyridyl]oxy]phenyl] ethyl]-1 – methyl-pyrazolo[4,3-d]pyrimidin-7-amine (1-10) To a solution of 2-[3-methoxy-4-[[2-(trifluoromethyl)-4-pyridyl]oxy]phenyl]ethanamine (0.39 g, 1 .2 mmol) in acetonitrile (30 ml.) was added triethylamine (1 .5 g, 4.8 mmol). The solution was stirred for 5 min at room temperature at which time 7-chloro-1 -methyl-pyrazolo[4,3-d]pyrimidine (0.25 g, 1 .2 mmol) was added. The reaction mixture was stirred at room temperature overnight. Water was added and was extracted with ethyl acetate (3x). The combined organic layers were washed with water, dried over Na2S04 and concentrated in vacuo. The residue was purified by HPLC to provide 85 mg (0.19 mmol, 17%) of the product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,923282-39-7, 7-Chloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BASF SE; BASF SCHWEIZ AG; GRAMMENOS, Wassilios; CRAIG, Ian Robert; BOUDET, Nadege; MueLLER, Bernd; DIETZ, Jochen; LAUTERWASSER, Erica May Wilson; LOHMANN, Jan Klaas; MONTAG, Jurith; WO2013/113715; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 37482-64-7, 2-Chloro-4-ethoxy-6-methylpyrimidine, 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, Computed Properties of C7H9ClN2O, blongs to pyrimidines compound. Computed Properties of C7H9ClN2O

EXAMPLE 10 4-Ethoxy-2-(1-imidazolyl)-6-methylpyrimidine In anhydrous tetrahydrofuran, 173 mg of 2-chloro-4-ethoxy-6-methylpyrimidine was substituted with 68 mg of imidazole. The reaction mixture was treated according to the procedure of Example 5 to yield 103 mg of 4-ethoxy-2-(1-imidazolyl)-6-methylpyrimidine, recrystallized from a mixture of n-hexane and ethyl acetate, having a melting point of 115.5-116 C. NMR(CDCl3)delta: 1.13(3H,t,J=8 Hz), 2.44(3H,s), 4.50(2H,q,J=8 Hz), 6.43(1H,s), 7.20(1H,s), 7.90(1H,s), 8.63(1H,s).

The synthetic route of 37482-64-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nissin Shokuhin Kabushiki Kaisha; US4849424; (1989); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 71470-41-2, 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 71470-41-2, name is Ethyl 4-aminopyrimidine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Example 264a 2-(4-Aminopyrimidin-2-yl)propan-2-ol 264a To a solution of ethyl 4-aminopyrimidine-2-carboxylate (840 mg, 5.0 mmol) in anhydrous tetrahydrofuran (50 mL) cooled at -20 C was added a solution of methylmagnesium bromide in THF (8.5 mL, 25.0 mmol, 3.0 M) over a period of 5 minutes. The reaction mixture was stirred at 0C for another 2 h. It was then quenched with saturated NH4Cl (20 mL) and concentrated under reduced pressure. The residue was extracted with ethyl acetate (5 X 40 mL). The combined organic layer was dried over anhydrous Mg2SO4, filtered, and evaporated under reduced pressure. The residue was purified by reverse-phase Combiflash to afford 264a as yellow solid (240 mg, 32%) MS-ESI: [M+H]+ 154.1

According to the analysis of related databases, 71470-41-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4763-35-3, 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.4763-35-3, name is 2-Amino-5-methoxypyrimidin-4(1H)-one, molecular formula is C5H7N3O2, molecular weight is 141.13, as common compound, the synthetic route is as follows.

Step 3. Into a 100 mL round bottom flask equipped with a magnetic stir bar was placed 2-Amino-4-hydroxy-5-methoxy-pyrimidine (500 mg, 3.54 mmol), anhydrous DMF (30 mL), AA-13 (1 .27 g, 5.31 mmol), DBU (2.12 mL, 14.17 mmol), and BOP (1 .96 g, 4.43 mmol). The reaction mixture was allowed to stir at room temperature for 30 minutes then at 50C for 16 hours. The solvent was removed under reduced pressure and the residue was partitioned between brine and ethyl acetate. The organic layers were combined, dried (magnesium sulfate), the solids were removed via filtration, and the solvents of the filtrate were removed under reduced pressure. The crude was purified via reverse phase liquid chromatography (RP Vydac Denali C18 – 10 m, 250 g, 5 cm. Mobile phase 0.25% NH4HCO3 solution in water, methanol), the best fractions were pooled, the solvents were removed under reduced pressure to afford 89.

The chemical industry reduces the impact on the environment during synthesis 4763-35-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN R&D IRELAND; MC GOWAN, David; RABOISSON, Pierre Jean-Marie Bernard; EMBRECHTS, Werner; JONCKERS, Tim, Hugo, Maria; LAST, Stefaan, Julien; PIETERS, Serge, Maria, Aloysius; VLACH, Jaromir; WO2012/136834; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 15846-19-2, name is 4-Chloro-6-methoxypyrimidin-5-amine, the common compound, a new synthetic route is introduced below. SDS of cas: 15846-19-2

Prepared as described forN-cyclohexyl-4-iodopyridin-3-amine (Intermediate 17), to a stirred solution of 4-chloro-6-methoxypyrimidin-5-amine (CAS 15846-19-2; 200 mg, 1.25 mmol) and cyclopentanone (CAS 120-92-3; 0.33 mL, 3.76 mmol) in anhydrous DCM (6 mL) under an atmosphere of N2at 0 C was added dropwise T1CI4solution (iM in DCM, 1.4 mL, 1.38 mmol). The reaction was stirred at room temperature for 2 h. Sodium triacetoxyborohydride (797 mg, 3.76 mmol) was added portionwise and the reaction stirred at room temperature for 16 h. The crude product was purified by column chromatography (silica, 0-50% EtOAc / petroleum ether) to afford the title compound. 1H NMR (400 MHz, CHLOROFORM-d) 8 ppm 1.33 – 1.53 (m, 2 H) 1.55 – 1.82 (m, 4 H) 1.83 – 2.00 (m, 2 H) 3.73 (d, J=9 Hz, 1 H) 4.04 (s, 3 H) 4.18 – 4.42 (m, 1 H) 8.08 (s, 1 H) MS ES+: 228

The synthetic route of 15846-19-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAVENPORT Richard; DUNN Jonathan; FARNABY William; HANNAH Duncan; HARRISON David; WRIGHT Susanne; WO2015/198046; A1; (2015);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 134221-52-6 ,Some common heterocyclic compound, 134221-52-6, molecular formula is C7H7ClN2O3, 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.

To a stirred solution of 2-methyl-4-morpholin-4-yl-6-nitro-phenyl amine (0.290 g, 1.22 mmol) in methanol (40 mL) was added 10% palladium on carbon (180 mg) and the suspension flushed well with nitrogen, followed by hydrogen. The resulting suspension was stirred 8 hours at room temperature under an atmosphere of hydrogen (ca. 1 atm). The resulting suspension was filtered under nitrogen through a pad of Celite and washed with methanol (50 mL). This solution was cooled down to 0 C. and the 4-chloro-2,6-dimethoxy-pyrimidine-5-carbaldehyde (N. Ple et al. J. Heterocyclic Chem., 28, 283, 1991 (0.272 g, 1.34 mmol) in methanol (50 ml) was added and the reaction mixture as stirred exposed to air at 23 C. for 18 hours. MeOH was evaporated in vacuo and the crude material was purified on silicagel dry column using CH2Cl2: Isopropanol (9:1) to give the title compound as a yellow solid. (0.304 g, 64%), HPLC: 98% (220 nm), LCMS (+ESI, M+H+) m/z 390, IR (KBr, cm-1) 3421, 2955, 2854, 1602, 1540, 1385; 1H NMR (400 MHz, DMSO) delta 6.70 (br s, 2H), 3.87 (s, 3H), 3.80 (s, 3H), 3.63 (m, 4H), 2.94 (m, 4H), 2.34 (s, 3H);

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. 134221-52-6, 4-Chloro-2,6-dimethoxypyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Beaulieu, Francis; Marinier, Anne; Ouellet, Carl; Roy, Stephan; Wittman, Mark D.; US2005/54655; (2005); A1;,
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. 3438-55-9, name is 5-Bromo-4-chloro-6-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Bromo-4-chloro-6-methylpyrimidine

The (+/-)-(3aR,4S,6R,6aS)-6-amino- in ethanol (9.0 ml, 0.5 M)2,2-Dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-ol (T-1)(786 mg, 4.54 mmol), 5-bromo-4-chloro-6-methylpyrimidine(1.04 g, 4.99 mmol) and trimethylamine (0.822 ml, 5.9 mmol)The mixture was heated to 80 C for 20 hours.The crude reaction mixture was concentrated to a solid and then purified by chromatography on a gradient of 0% to 100% EtOAc in heptane to give T-2 as a white solid, 1.35 g (87% 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, 3438-55-9, 5-Bromo-4-chloro-6-methylpyrimidine.

Reference:
Patent; PFIZER INC.; KUMPF, ROBERT ARNOLD; MCALPINE, INDRAWAN JAMES; MCTIGUE, MICHELE ANN; PATMAN, RYAN; RUI, EUGENE YUANJIN; TATLOCK, JOHN HOWARD; TRAN-DUBE, MICHELLE BICH; WYTHES, MARTIN JAMES; (445 pag.)TW2018/2074; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 74840-34-9, name is 4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 74840-34-9

0.35g (1.71mmol) of 4-chloro-2-(methylsulfanyl)pyrimidine-5-carboxylic acid was dissolved in 20mL dichloromethane solvent, 0.37g (2.94mm0l) oxalyl chloride was added, 1 drop DMF, stirred at room temperature for 6h and then under reduced pressure Evaporation of solvent and excess oxalyl chloride gave a yellow solid;This was dissolved in 20 mL of dichloromethane and then 0.22 g (1.21 mmol) of 5-[(methylamino)methyl]-1H-imidazole-4-ethylformate and 0.21 g (2.05 mmol) of triethylamine were added and stirred at room temperature After the reaction, it was poured into 30 mL of saturated sodium bicarbonate solution and extracted with dichloromethane (20 mL × 2). The combined organic phase was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure to give 5-((4-chloro-N-methyl-2-(methylsulfanyl)pyrimidine-5-carboxamido)methyl)-1H-imidazole-4-ethylformate was used directly in the next reaction.A solution of ethyl 5-((4-chloro-N-methyl-2-(methylsulfanyl)pyrimidine-5-carboxamido)methyl)-1H-imidazole-4-ethylformate in 20 mL of acetonitrile was added 0.58 g 4.22 mmol) anhydrous potassium carbonate and stirred at room temperature until the reaction was completed. The solvent was distilled off under reduced pressure.The residue was dissolved in 20 mL of methylene chloride, washed with 30 mL of saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was purified by column chromatography (CH2C12: CH3COCH3 = 10: 1) to give a white solid The yield is 60percent.

With the rapid development of chemical substances, we look forward to future research findings about 74840-34-9.

Reference:
Patent; Beijing Normal University; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Zhang Zhanbin; Yu Gang; Li Yi; Xiao Guiying; Cao Yanqing; Su Ruibin; Zheng Zhibing; Zhou Xinbo; (12 pag.)CN107312012; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia