Day: October 27, 2020

7226-23-5 , The common heterocyclic compound, 7226-23-5, name is 1,3-Dimethyltetrahydropyrimidin-2(1H)-one, molecular formula is C6H12N2O, 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 35 1-[3-Cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionyl]-3-methyl Urea A solution of diisopropylamine (17.1 mL, 122.21 mmol) in dry tetrahydrofuran (55 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (18 mL) was cooled to -78 C. under nitrogen and then treated with a 10M solution of n-butyllithium in hexanes (12.2 mL, 122.21 mmol). The yellow reaction mixture was stirred at -78 C. for 30 min and then treated dropwise with a solution of 4-iodophenylacetic acid (15.25 g, 58.19 mmol) in dry tetrahydrofuran (55 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (18 mL). The reaction mixture turned dark in color and was allowed to stir at -78 C. for 45 min, at which time, a solution of iodomethylcyclopentane (13.45 g, 64.02 mmol) in a small amount of dry tetrahydrofuran was added dropwise. The reaction mixture was allowed to warm to 25 C. where it was stirred for 42 h. The reaction mixture was concentrated in vacuo to remove tetrahydrofuran and then quenched with a 10% aqueous hydrochloric acid solution (100 mL). The resulting aqueous layer was extracted with ethyl acetate (3*200 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1*200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid (13.97 g, 70%) as a cream solid: mp 121-122 C.; EI-HRMS m/e calcd for C14H17IO2 (M+) 344.0273, found 344.0275.

According to the analysis of related databases, 7226-23-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Corbett, Wendy L.; Haynes, Nancy-Ellen; Sarabu, Ramakanth; US2002/2190; (2002); 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. 372118-67-7, name is Pyrimidin-2-ylmethanamine hydrochloride, molecular formula is C5H8ClN3, 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. 372118-67-7

A mixture of methyl amino pyrimidine (250 mg, 1 eq, 1.718 mmol), FMOC-NCS (531 mg, 1.1 eq, 1.9 mmol) and diisopropyl ethyl amine (0.3 ml, 1 eq, 1,718 mmol) was stirred in 1,4-dioxane (10 ml) at 25 C overnight under argon atmosphere. A solid separated out from mixture was filtered and washed with water and ethyl acetate, and dried under high vaccuum. Yield 658 mg, 98%. Solid obtained from the reaction (658 mg, 1 eq, 1.2 mmol) was stirred in piperidine (3 ml) and dichloromethane (15 ml) at 25 C overnight. A solid percipitate was collected by filtration and washed with dichloromethane and water to give a white solid. Yield 289 mg, 98%.LCMS, 169 (MH+).

The chemical industry reduces the impact on the environment during synthesis 372118-67-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BARUCH S. BLUMBERG INSTITUTE; DU, Yanming; LU, Huagang; ROGOWSKY, John; KINNEY, William, A.; CUCONATI, Andrea; (76 pag.)WO2018/13508; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding some certain compound to certain chemical reactions, such as: 1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine, 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 1780-26-3. 1780-26-3

20 mmol of 4,6-dichloro-2-methylpyrimidine, 40mmol K3PO4 was dissolved in 100mL N,N-dimethylacetamide, stirring,0.3 mmol of 1-butyl-3-methylimidazolium glycinate and 22 mmol of N-hydroxyethylpiperazine were added in this order, and the mixture was reacted at 80 C for 2 h, and then cooled to room temperature. Add 22 mmol of 2-amino-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide, The reaction was continued at 80 C for 3 h. After the reaction was completed, it was cooled to room temperature and poured into ice water. It was extracted with ethyl acetate three times (3¡Á50 mL), and the ethyl acetate phase was combined. The organic layer was washed with anhydrous Na2SO4 to give a crude product. The crude product was added to 100 mL of an 80% aqueous ethanol solution, and 2 g of activated carbon was added thereto with stirring. After refluxing for 30 min, it was filtered while hot, and the filtrate was recrystallized overnight and filtered. The filter cake was washed with ice-cold 80% aqueous ethanol and dried. That is, 8.72 g of a white solid was obtained, the yield was 89.31%, and the purity was 99.94%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1780-26-3.

Reference:
Patent; Shandong Luoxin Pharmaceutical Group Co., Ltd.; Shandong Luoxin Pharmaceutical Group Hengxin Pharmaceutical Co., Ltd.; Shandong Yuxin Pharmaceutical Co., Ltd.; Li Mingjie; Li Chenglong; Li Cheng; (12 pag.)CN109678853; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

696-82-2, 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. 696-82-2, name is 2,4,6-Trifluoropyrimidine. A new synthetic method of this compound is introduced below.

Example 1 0.5 mol of fluorine in the form of a 30% by volume mixture with helium was introduced into a suspension of 29.0 g (0.216 mol) of 2,4,6-trifluoropyrimidine, 21 g of sodium fluoride (0.5 mol) and 250 ml of trichlorofluoromethane at a temperature of -78 C. The rate of introduction was 0.15 mol of fluorine per hour. After the introduction was complete, the reaction mixture was filtered and 21.0 g of tetrafluoropyrimidine (=64% of theory) were obtained from the filtrate by distillation.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,696-82-2, 2,4,6-Trifluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Aktiengesellschaft; US5145961; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

776-53-4, 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 776-53-4, name is Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 (4-Amino-2-methanesulfanyl-pyrimidin-5-yl)-methanol A solution of 4-amino-2-methanesulfanyl-pyrimidine-5-carboxylic acid ethyl ester (13.36 g, 63 mmol) in 250 mL of tetrahydrofuran is added dropwise to a room temperature suspension of lithium aluminum hydride (3.82 g, 100 mmol) in 250 mL of tetrahydrofuran. After 30 minutes, the reaction is cooled to 0 C., and isopropyl alcohol is added until bubbling diminishes. The reaction is quenched with 15 mL of water, 15 mL of 15% NaOH, and 50 mL of water, and the mixture is stirred for 1 hour. The white precipitate is removed by filtration and washed with ethyl acetate. The filtrate is concentrated in vacuo and 3:1 hexane:ethyl acetate is added. The solids are collected, washed with 3:1 hexane:ethyl acetate, followed by hexane. The solid is dissolved in ethyl acetate, and the solution is dried over magnesium sulfate. Filtration followed by concentration in vacuo gives 8.14 g (76%) of (4-amino-2-methanesulfanyl-pyrimidin-5-yl)-methanol. Analysis calculated for C6H9N3OS: C, 42.09: H, 5.30: N, 24.54. Found: C, 42.31: H, 5.24: N, 24.27.

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 776-53-4, Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate.

Reference:
Patent; Booth, Richard John; Dobrusin, Ellen Myra; Josyula, Vara Prasad Venkata Nagendra; McNamara, Dennis Joseph; Toogood, Peter Laurence; US2003/73668; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine. A new synthetic method of this compound is introduced below., 113583-35-0

EXAMPLE 1 Preparation of methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-(1-pyrrolidinyl)picolinate (Compound No. 317) 1.55 g (7 mmol) of methyl 3-hydroxy-6-(1-pyrrolidinyl)picolinate, 1.83 g (8.4 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 0.96 g (7 mmol) of potassium carbonate were added to 50 ml of DMF and reacted at 100C for 3 hours. After completion of the reaction, the reaction product was poured into ice water, extracted with ethyl acetate, washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The solvent was distilled off, and the residue was crystallized from diisopropyl ether to obtain the desired product. Amount: 2.11 g (yield: 84%), melting point: 151-153C

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113583-35-0, 2-Methanesulfonyl-4,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; KUMIAI CHEMICAL INDUSTRY CO., LTD.; IHARA CHEMICAL INDUSTRY Co., Ltd.; EP567133; (1993); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

7752-82-1, 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 7752-82-1, name is 5-Bromopyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Sodium carbonate (0.636 g, 6.0 mmol) in water (2.0 mL) was added to a mixture of 5- bromopyrimidin-2-amine (0.348 g, 2.0 mmol), [3-(tert-butoxycarbonyl)phenyl]boronic acid (0.533 g, 2.4 mmol) and tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) in ethanol (3.0 mL) and toluene (3.0 mL). The resulting mixture was heated at 120 0C for 3 h. The mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was treated with methanol. The precipitate was filtered and dried to give the product (399 mg, 73.5%). 272.1.

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 7752-82-1, 5-Bromopyrimidin-2-amine.

Reference:
Patent; INCYTE CORPORATION; ZHUO, Jincong; METCALF, Brian; WO2008/64157; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

147118-40-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 147118-40-9 as follows.

Chromatographic column:LiChrospher 100 DIOL 10 mum 250 x 20mm Mobile phase A:diisopropyl ether (DIPE) Mobile phase B:1,5percent isopropanol, 98,5percent DIPE Flow rate:60 ml/min Detection:UV, 345 nm Injection volume:60 ml 1,5 g of the crude sample (assay 70percent) is dissolved in 60 ml of diisopropylether. The obtained solution is loaded on a chromatographic column, previously conditioned with mobile phase A. After the sample load the chromatographic column is eluted with mobile phase B. A central portion (ca 100 ml) of main peak is collected. The obtained fraction is pure MER, with ca 99,8 percent chromatographic purity, and ca 6-7percent of enantiomer, as shown on Fig.3

The chemical industry reduces the impact on the environment during synthesis 147118-40-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; LEK Pharmaceuticals d.d.; EP2022784; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

672-41-3 ,Some common heterocyclic compound, 672-41-3, molecular formula is C5H4F3N3, 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 solution of 6-(trifluoromethyl) pyrimidin-4- amine (1.0 g, 6.2 mmol) in DMF (30 mE) was added NBS (1.2 g, 6.8 mmol). The mixture was heated to 70 C. for 1 hout The reaction mixture was cooled to it, diluted with H20, and extracted with EtOAc (x2). The combined organic extracts were washed with brine; dried (Na2504) and concentrated in vacuo. The crude product was triturated in DCM to obtain title compound as white solid (1.38 g, 93%).

According to the analysis of related databases, 672-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Laforteza, Brian Ngo; Lebold, Terry Patrick; Ravula, Suchitra; Savall, Brad M.; Shireman, Brock T.; (70 pag.)US2018/111942; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

56-09-7, 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. 56-09-7, name is 2-Amino-6-hydroxypyrimidin-4(3H)-one, molecular formula is C4H5N3O2, 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.

A mixture of 2-amino-pyrimidine-4,6-diol 28.00g (0.22mol), thionyl chloride 80ml (1.1mol) into 250ml 4-neck flask, heated to reflux for 4h.After completion of the reaction, the heat is turned off, cooled to room temperature, the reaction was quenched by slowly poured into ice water.In this case large amount of solid precipitated, filtered off with suction, the filter cake was rinsed with potable water to pH 7.The wet cake at 60 deg.] C blast drying to constant weight, to give a pale yellow product 33.45g, this step a yield of 92.7%, HPLC purity was 99.1%.

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. 56-09-7, 2-Amino-6-hydroxypyrimidin-4(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Weihai Disu Pharmaceutical Co., Ltd.; Disha Pharmaceutical Group Co., Ltd.; Liu Chao; Ge Zhixin; Li Tingyi; Miao Huaming; Cai Yahui; (13 pag.)CN109456329; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia