Tag: M.W:100-200

Synthetic Route of 4316-97-6 ,Some common heterocyclic compound, 4316-97-6, molecular formula is C5H4Cl2N2, 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.

[00434] Step 2: Synthesis of 4,6-dichloro-2-(5-methoxy-2-(trifluoromethyl)phenyl)-5- methylpyrimidine. To a solution of 2-bromo-4-methoxy-1-(trifluoromethyl)benzene (5.0 g, 19.6 mmol) in dry THF (50 mL) stirred at -78 C under nitrogen atmosphere, was added n- Butyl lithium (8.9 mL, 2.4 M in hexane, 21.4 mmol) over a period of 5 minutes, the mixture was stirred for another 10 minutes at the same temperature before 4,6-dichloro-5- methylpyrimidine (4.5 g, 27.9 mmol) in THF (5 mL) was added slowly over 5 minutes. The resulting mixture was stirred at -78 C for 30 minutes, then quenched with HOAc (1.5 mL) and warmed to 0 C slowly. DDQ (6.6 g, 29.1 mmol) was then added portion wise and the resulting mixture was stirred at 0 C for 30 minutes, diluted with CH2Cl2(100 mL), washed with 10% NaOH (50 mL x 2) and brine (100 mL); the organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified silica column chromatography with (petroleum ether/EtOAc = 100/1 to 30/1) to render 4,6-dichloro-2-(5-methoxy-2- (trifluoromethyl) phenyl)-5-methylpyrimidine (1.0 g, 21% yield). ESI-LCMS (m/z): 337.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4316-97-6, its application will become more common.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; MORADEI, Oscar, Miguel; SHAPIRO, Gideon; JIN, Lei; BABINE, Robert, E.; (495 pag.)WO2016/44641; (2016); A2;,
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. 14161-09-2, name is 2-(Methylsulfonyl)pyrimidine, the common compound, a new synthetic route is introduced below. Quality Control of 2-(Methylsulfonyl)pyrimidine

Example 123 N-(2-((5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-yl)oxy)ethyl)pyrimidin-2-amine 2-((5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-yl)oxy)ethanamine hydrochloride (57 mg, 0.152 mmol) and 2-(methylsulfonyl)pyrimidine (96 mg, 0.608 mmol) were dissolved in 2 mL ethanol in a microwave vial. Triethylamine (0.1 mL) was added and the mixture was heated at 120 C. for one hour in the microwave. All volatiles were removed under vacuum and the residue was purified on 12 g silica gel with 0-100% ethyl acetate in hexane to give the title compound (40 mg, 0.096 mmol). MS: 417 (MH+).

The synthetic route of 14161-09-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Graupe, Michael; Lu, Yafan; Zablocki, Jeff A.; US2015/175560; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3524-87-6, Adding some certain compound to certain chemical reactions, such as: 3524-87-6, name is 6-Methylpyrimidin-4(3H)-one,molecular formula is C5H6N2O, 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 3524-87-6.

To 70 g (0.64 mol) A-1 in acetic acid is added 127 g (0.56 mol) NIS portion wise at RT within 15 min. The reaction is stirred at RT until all starting material is consumed (30 h). The reaction mixture is diluted with water and the solid product is filtered off, washed with an aqueous sodium thiosulfate solution to remove excess iodine and dried in vacuo. Yield: 90 g (60%).

According to the analysis of related databases, 3524-87-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WUNBERG, Tobias; KRAEMER, Oliver; van der VEEN, Lars; US2013/23533; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1193-24-4 ,Some common heterocyclic compound, 1193-24-4, molecular formula is C4H4N2O2, 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 cooled (0 C.) phosphorus oxychloride (20.0 mL, 215 mmol, 4.8 equiv.) was added DMF (6.4 mL, 83 mmol, 1.9 equiv) dropwise over 3 min. The reaction mixture was stirred for fifteen min and the ice bath was removed. 4,6-Dihydroxypyrimidine (5.0 g, 44.6 mmol, 1.0 equiv.) was added and the reaction mixture was heated to 130 C. and stirred for 3.5 hr. The mixture was cooled to RT and concentrated. Ice was slowly added to the dark brown residue, followed by 600 mL of ice water. The aqueous mixture was extracted with diethyl ether (5¡Á100 mL), and the organic extracts were washed with aqueous saturated NaHCO3 (2¡Á100 mL) and brine (100 mL), and dried over anhydrous sodium sulfate and concentrated in vacuo to provide Compound 15 (4.42 g, 57%) as a crude orange solid, which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1193-24-4, its application will become more common.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2009/36419; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 62802-38-4, 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.62802-38-4, name is 5-Bromo-2-fluoropyrimidine, molecular formula is C4H2BrFN2, molecular weight is 176.9745, as common compound, the synthetic route is as follows.

To a solution of 5-ethyl-4-nitro-1H-pyrazole (350 mg, 2.5 mmol) and 3,4- dihydro-2H-pyran (319 mg, 3.8 mmol) in DCM (20 mE) at 0 C was addedp-TsOH(43 mg, 0.25 mmol), and the mixture was stirred at 0 C for lh and then at rt overnight. DCM (100 mL) was added, and the mixture was washed with water and brine, dried over Na2 SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with petroleum ether/EtOAc (10:1 to 1:1) to afford a mixture of 3-ethyl-4-nitro-1- (tetrahydro-2H-pyran-2-yl)- 1JJ-pyrazole and 5 -ethyl-4-nitro- 1 -(tetrahydro-2H-pyran-2-yl)- 1H- pyrazole.; To a solution of 3-ethyl-4-nitro-1-(tetrahydro-2H-pyran-2-yl)-1JJ-pyrazole and5-ethyl-4-nitro-1-(tetrahydro-2H-pyran-2-yl)-1ff-pyrazole (557 mg, 2.5 mmol) in MeOH (20 mE) at 0C was added 10 % Pd/C (50 mg), and the mixture was stirred under H2 overnight at rt. DCM (20 mE) was added and the mixture was filtered through the Celite. The filtrate was concentrated under reduced pressure to afford a mixture of 3-ethyl-1-(tetrahydro-2H-pyran-2- yl)- 1H-pyrazol-4-amine and 5-ethyl-i -(tetrahydro-2H-pyran-2-yl)- 1H-pyrazol-4-amine, which was used in the next step without further purification; To a solution of 3-ethyl-1-(tetrahydro-2H-pyran-2-yl)-iH-pyrazol-4-amine, – ethyl-1-(tetrahydro-2J1-pyran-2-yl)-1H-pyrazol-4-amine (252 mg, 1.03 mmol) and 5-bromo-2- fluoro-pyrimidine (166 mg, 0.94 mmol) in DMSO (7 mL) was added DIEA (243 mg, 1.88 mmol), and the mixture was stirred at 100 C for 1.5 h. DCM (100 mE) was added, and the mixture was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with petroleum ether EtOAc (10:1 to 2:1) to afford a mixture of 5-bromo-N-(3 -ethyl-i -(tetrahydro-2H-pyran-2-yl)- 1H-pyrazol-4-yl)pyrimidin-2-amine and 5-bromo-N-(5-ethyl- i -(tetrahydro-2H-pyran-2-yl)- 1H- pyrazol-4-yl)pyrimidin-2-amine.

The chemical industry reduces the impact on the environment during synthesis 62802-38-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PLEXXIKON INC.; HOLLADAY, Mark W.; LIU, Gang; (267 pag.)WO2017/19804; (2017); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 13223-25-1, 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.13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, molecular weight is 174.59, as common compound, the synthetic route is as follows.

EXAMPLE 9 Preparation of methylthioethyl 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate (Compound No. 2) Methylthioethyl 2,6-dihydroxybenzoate (4.5 g) was dissolved in DMF, and 60% sodium hydride (1.6 g) was added thereto. Then, 2 chloro-4,6-dimethoxypyrimidine (3.5 g) was added thereto, and the mixture was heated and reacted at a temperature within a range of from 90 to 10 C. for two hours. The reaction solution was poured into ice water and then extracted twice with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate. After removing inorganic substances by filtration, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to obtain the above identified compound as a colorless viscous liquid. (etaD20: 1.5706).

The chemical industry reduces the impact on the environment during synthesis 13223-25-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US4906285; (1990); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 39906-04-2, 4,6-Dichloro-2-methylpyrimidin-5-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, HPLC of Formula: C5H5Cl2N3, blongs to pyrimidines compound. HPLC of Formula: C5H5Cl2N3

NH3 (g) was bubbled into EtOH (60 mL) at -40 C for 0.5 h (15 Psi). Then 4,6- dichloro-2-methyl-pyrimidin-5-amine (5 g, 28.09 mmol, 1 eq) was added at 18 C, and the result reaction mixture was stirred at 120 C for 13.5 hr (15 Psi). The reaction mixture was concentrated under reduced pressure to remove EtOH. Compound 6-chloro-2-methyl- pyrimidine -4, 5-diamine (I-791) (5.8g) was obtained as a yellow solid. LCMS m/z 158.8 (M+1)+.

The synthetic route of 39906-04-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SITARI PHARMA, INC.; CAMPBELL, David; CHAPMAN, Justin; CHEUNG, Mui, H.; DIRAIMONDO, Thoams, R.; DURON, Sergio, G.; (615 pag.)WO2020/33784; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1195-08-0 ,Some common heterocyclic compound, 1195-08-0, molecular formula is C5H4N2O3, 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.

Amine 2.2; 5-[(cyclopropylamino)methyl]-l ,3-bis(3-methoxypropyl)pyrimidine-2,4(lH,3/i)- dione; Step 1 : l,3-bis(3-methoxypropyl)-2,4-dioxo-l,2,3,4-tetrahvdropyrimidine-5-carbaldehvde; To a solution of 2,4-dioxo-l,2,3,4-tetrahydropyrimidine-5-carbaldehyde (1 eq.) and l-bromo-3-methoxypropane (2.2 eq.) at rt in DMF (0.36 M) was added DBU (2.2 eq.). The reaction mixture was stirred at rt 3 days, concentrated in vacuo, and the residue purified by flash chromatography (SiO2; EtOAc) to afford the title compound.

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. 1195-08-0, 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2009/70869; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 17321-93-6, 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 17321-93-6, name is 2-Amino-5-bromo-4-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5-bromo-4-methylpyrimidine-2-ylamine (5.0 g, 26 mmol), potassium acetate (7.83 g, 79.8mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (7.43 g,29.2 mmol) in dioxane (140 mL) was stirred for 20 min under nitrogen. 1,1?-bis(diphenylphosphino)ferrocene palladium (II) chloride dichloromethane adduct (1.08 g, 1.33 mmol) was added to the reaction mixture. The reaction mixture was heated to 115¡ã C. for 18 h under nitrogen. Upon completion, the mixture was cooled and EtOAc was added. The resulting mixture was sonicated and filtered. Additional EtOAc was used to wash the solid. The combined organic extracts were washed with water, dried over MgSO4, filtered and concentrated. The crude was purified by chromatography eluting with 20~100percent EtOAc/hexane to yield 4.5 g of 4-methyl-5-(4,4,5,5-tetramethyl (1,3,2-dioxaborolan-2-yl))pyrimidine-2-ylamine 26 (yield: 74percent). 1H-NMR (DMSO, 400 MHz): delta 8.28 (s, 1H), 6.86 (br s, 2H), 2.35 (s, 3H), 1.25 (s, 12H). MS (ESI) m/e (M+H+) 236.15, 154.07.

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 17321-93-6, 2-Amino-5-bromo-4-methylpyrimidine.

Reference:
Patent; Genentech, Inc.; Heald, Robert Andrew; McLean, Neville James; US2014/65136; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 4316-94-3, 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.4316-94-3, name is 6-Chloro-5-nitropyrimidin-4-amine, molecular formula is C4H3ClN4O2, molecular weight is 174.55, as common compound, the synthetic route is as follows.

General procedure: 6-Chloro-5-nitropyrimidine-4-amine (0.5mmol), amine (1.5mmol), Pd2(dba)3 (0.01mmol), R-BINAP (0.03mmol) and potassium carbonate (0.7mmol) were dissolved in acetonitrile (5mL). The solution was stirred at room temperature for 3.5h under an argon atmosphere. The resulting reaction mixture was treated with saturated brines (50mL) and extracted with acetonitrile (3¡Á25mL), and dried with anhydrous Na2SO4. The anhydrous Na2SO4 was removed by filtration and the filtrate was concentrated. The residue was washed with ethyl acetate (3¡Á2mL) and diethyl ether (3¡Á2mL), filtered and dried under vacuum.

The chemical industry reduces the impact on the environment during synthesis 4316-94-3, I believe this compound will play a more active role in future production and life.

Reference:
Article; Liu, Meng-Meng; Mei, Qiong; Zhang, Yi-Xiao; Bai, Peng; Guo, Xiang-Hai; Chinese Chemical Letters; vol. 28; 3; (2017); p. 583 – 587;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia