Day: April 26, 2021

Application of 4994-86-9 , The common heterocyclic compound, 4994-86-9, name is 4-Chloro-2-methylpyrimidine, molecular formula is C5H5ClN2, 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 4-chloro-2-methylpyrimidine (1 g, 7.77 mmol) in 1, 4- dioxane (30 mL) under a argon atmosphere were added diisopropyl ethyl amine (1.35 g, 10.50 mmol) and tert-butyl piperidin-4-ylcarbamate (1.7 g, 8.55 mmol) at RT. The reaction mixture was stirred at 150 C for 3 h. After consumption of the starting material (monitored by TLC), the reaction was diluted with water (50 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified through silica gel column chromatography using 5% MeOH: DCM to afford tert-butyl (1 -(2-methylpyrimidin-4-yl) piperidin-4-yl) carbamate (1.5 g, 66%) as an off-white solid. ?H-NMR (DMSO-d6, 500 MHz): oe 8.04-8.02 (m, 1H), 6.83- 6.82 (m, 1H), 6.61-6.60 (m, 1H), 4.27-4.25 (m, 2H), 3.51 (s, 1H), 2.96-2.91 (m, 2H), 2.33 (s, 3H), 1.77-1.74 (m, 2H), 1.37 (s, 9H), 1.28-1.22 (m, 2H); LC-MS: 293.3 (M+1); (column; XBridge C-18 (50 x 3.0 mm, 3.5 jim); RT 2.90 mm. 5 mM NH4OAc: ACN; 0.80 mL/min); TLC: 50% EtOAc:hexanes (R1: 0.2).

The synthetic route of 4994-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66696; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3977-29-5, 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. 3977-29-5, name is 2-Amino-6-methylpyrimidin-4(1H)-one. A new synthetic method of this compound is introduced below.

In a two-neck round-bottom flask containing precooled sulfuricacid (3 mL) was added 2-amino-4-hydroxy-6-methylpyrimidine(1) (100 mg, 0.8 mmol). An effective temperature control isrequired to the nitration occur properly. Nitric acid (0.2 mL,3.0 mmol) was added to the solution dropwise maintaining thetemperature below 6 C using an ice bath. The mixture waswarmed to room temperature and stirred for 3 h. The reaction mixturewas added in cold ethyl ether (10 mL), remaining the temperaturebelow 10 C. The precipitate was filtered and dissolved inboiling 1 mol/L NaOH solution. Acetic acid was added to the solutionfor precipitation of the product (pH among 6-8). The solid wasfiltered under vacuum, washed with water (2 1 mL) and dried invacuum for 8 h. The pyrimidinone 2 was obtained in 69% yield(117 mg)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3977-29-5, its application will become more common.

Reference:
Article; Rodrigues, Marili V.N.; Barbosa, Alexandre F.; Da Silva, Julia F.; Dos Santos, Deborah A.; Vanzolini, Kenia L.; De Moraes, Marcela C.; Correa, Arlene G.; Cass, Quezia B.; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 226 – 231;,
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. 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H2Cl2N4

Compound 4 (1.5 g, 7.9 mmol),Toluenesulfonic acid (752 mg, 3.96 mmol) was dissolved in THF (30 ml) and DCM (30 ml)Of the mixture,Further 3,4-dihydropyran (2 g, 23.7 mmol) was added,Stir at room temperature 22h,TLC detection (PE: EA = 20: 1),Raw material reaction is complete,Spin drying solvent,Column chromatography (PE: EA = 50: 1) afforded 5 (1.2 g) as a white solid,Yield 54.5%.

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, 42754-96-1, 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Patent; Sichuan Baili Pharmaceutical Co., Ltd.; Wu, Yong; Zhu, Yi; Hai, Li; Wang, Yiqian; Li, Jie; (22 pag.)(2016);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 53554-29-3, Adding some certain compound to certain chemical reactions, such as: 53554-29-3, name is Ethyl 2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate,molecular formula is C8H10N2O3S, 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 53554-29-3.

Ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate (6; 10 g;46.7 mmol) was dissolved in a mixture of dioxan and chloroform (1:1;262 mL). Reaction mixture was cooled up to -2C, treated with m-CPBA (60%; 20.14 g, 70.0 mmol) and stirred for 50 min at 0 C.Reaction mixture was quenched by 10% aq. sodium metabisulfite(262 mL), extracted with chloroform and washed with aq. 10% sodiumbicarbonate. The organic layer was dried over sodium sulfate (40 g) andthe solvent was evaporated under reduced pressure to obtain ethyl 4-hydroxy-2-(methylsulfinyl)pyrimidine-5-carboxylate as a white solid.(8.6 g, 80%), which was further used in the next step without purification.To the mixture of ethyl 4-hydroxy-2-(methylsulfinyl)pyrimidine-5-carboxylate (8.6 g; 37.4 mmol) and PTSA (7.82 g; 41.1 mmol), dissolvedin NMP (80 mL) was added 4-(methylsulfonyl)aniline (6.99 g;37.4 mmol), at RT. The reaction mixture was heated at 100-110 C for1-2 h. After completion of reaction, the mixture was diluted with waterand the compound was extracted in EtOAc. Organic layer was driedover sodium sulfate, filtered and concentrated under vacuum to affordthe crude product. Crude product was purified by flash chromatographyover silica gel (100-200 mesh) with 2% MeOH/CHCl3 to get the ethyl4-hydroxy-2-((4-((methylsulfonyl) oxy)phenyl)amino) pyrimidine-5-carboxylate (7) (9.9 g, 75%). 1H NMR (DMSO-d6, 400 MHz) delta ppm 1.26(t, J = 7.0 Hz, 3H), 3.48 (s, 3H), 4.20 (q, J = 6.8 Hz, 2H), 6.57 (d,J = 9.2 Hz, 2H), 7.34 (d, J = 8.8 Hz, 2H), 8.49 (s, 1H), 9.75 (s, 1H),11.25 (s, 1H): ESI-MS: m/z Calcd for C14H16N3O6S [M+1]+ 354.35,found 354.58.

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. 53554-29-3, Ethyl 2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Argade, Anil; Bahekar, Rajesh; Bandyopadhyay, Debdutta; Chatterjee, Abhijit; Desai, Jigar; Desai, Ranjit C.; Ghoshdastidar, Krishnarup; Gite, Archana; Gite, Sanjay; Kumar, Jeevan; Mahapatra, Jogeswar; Panchal, Nandini; Patel, Bhaumin; Patel, Dipam; Patel, Harilal; Patel, Hoshang; S, Sachchidanand; Soman, Shubhangi; Sundar, Rajesh; Bioorganic Chemistry; vol. 99; (2020);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 4316-97-6, Adding some certain compound to certain chemical reactions, such as: 4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine,molecular formula is C5H4Cl2N2, 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 4316-97-6.

A 20 ml. Biotage microwave tube was purged with nitrogen and charged with 4,6-dichloro-5-methylpyrimidine (0.600 g, 2.98 mmol) and te/t-butyl 4-hydroxypiperidine- 1-carboxylate (534 mg, 3.28 mmol). 1 ,4-Dioxane (14.9 ml.) was added, and the mixture was heated to 100 degrees Celsius. To the mixture was added sodium bis(trimethylsilyl)amide (3.58 ml_, 3.58 mmol, 1.0 M in tetrahydrofuran) drop-wise over 10 minutes. The mixture was stirred for 60 minutes, and then at room temperature for 12 hours. The reaction was quenched with water, and the aqueous layer was extracted three times with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and the filtrate was concentrated in vacuo. The crude material was purified via silica gel chromatography (40 g SiO2 column, 0-50 % ethyl acetate in heptane gradient) to afford the title compound (842 mg, 86 %).

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. 4316-97-6, 4,6-Dichloro-5-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; DAROUT, Etzer; DENINNO, Michael, Paul; FUTATSUGI, Kentaro; GUIMARAES, Cristiano, Ruch, Werneck; LEFKER, Bruce, Allen; MASCITTI, Vincent; MCCLURE, Kim, Francis; MUNCHHOF, Michael, John; ROBINSON, Ralph, Pelton, Jr.; WO2010/128414; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5305-45-3, 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 5305-45-3 as follows.

The white solid, 4,6-dichloro-5-pyrimidinecarbonitrile (5.82 g, 33.5 mmol) was dissolved in THF (66.9 mL) in a 500 mL of round-bottom flask and ammonia gas (0.570 g, 33.5 mmol) was bubbled through for 3 min every 10 min for 50 min with stirring. A white precipitate (ammonium chloride) was formed. The precipitate was filtered and washed with THF (100 mL). To the filtrate was added silica gel and concentrated under reduced pressure. The mixture was purified by column chromatography on a 120 g of Redi-Sep column using 0 to 100% gradient of EtOAc in hexane over 27 min and then 100% isocratic of EtOAc in hexane for 20 min as eluent to give 4-amino-6-chloropyrimidine-5-carbonitrile as an off-white solid. The off-white solid was suspended in EtOAc-hexane (1:1, 20 mL), filtered, washed with EtOAc-hexane (1:1, 30 mL), and dried to give 4-amino-6-chloro-5-pyrimidinecarbonitrile (B) as a white solid: 1H NMR (500 MHz, DMSO-d6) delta ppm 7.91-8.77 (3H, m); LC-MS (ESI) m/z 154.9 [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,5305-45-3, its application will become more common.

Reference:
Patent; AMGEN INC.; US2011/245257; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 90905-32-1, 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. 90905-32-1, name is 2-Methoxypyrimidine-5-carbaldehyde, molecular formula is C6H6N2O2, 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.

2-Benzyloxycarbonylamino-3-(2-methoxy-pyrimidin-5-yl)-acrylic acid methyl ester To a suspension of potassium t-butoxide (1.23 g) in methylene chloride (70 mL, -30 C.) was added a solution of N-benzyloxycarbonyl-alpha-phosphonoglycine trimethyl ester (3.63 g) in methylene chloride (15 mL). The resulting solution was stirred 5 min and treated with the 2-methoxy-pyrimidine-5-carbaldehyde (1.0 g) in methylene chloride (15 mL). After stirring for 1.5 h, the reaction was warmed to 0 C. and stirred 1 h. The reaction was quickly poured into a sep funnel containing ethyl acetate and water. Brine was added to aid in separation of the layers. The aqueous was extracted with ethyl acetate (3*) which were in turn washed with brine, dried over magnesium sulfate, and concentrated. The crude product was recrystallized from hot methanol to give 1.4 g of pure material. Mass spec.: 344.10 (MH)+.

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 90905-32-1, 2-Methoxypyrimidine-5-carbaldehyde.

Reference:
Patent; Chaturvedula, Prasad V.; Chen, Ling; Civiello, Rita; Conway, Charles Mark; Degnan, Andrew P.; Dubowchik, Gene M.; Han, Xiaojun; J. Jiang, Xiang Jun; Karageorge, George N.; Luo, Guanglin; Macor, John E.; Poindexter, Graham; Tora, George; Vig, Shikha; US2004/204397; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 934524-10-4, 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.934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C13H9Cl2N3O2S, molecular weight is 342.2, as common compound, the synthetic route is as follows.

To a solution of 8 (0.80 g, 4.26 mmol), 4-methylthiophene-2-boronic acid (0.60 g, 4.26 mmol) and Pd(PPh3)4 (0.49 g, 0.43 mmol) in DMF was added Na2CO3 (2.0 M, 3.6 mL). The reaction mixture was heated 1 h at 120 0C and then cooled to room temperature. The resulting mixture was filtered through a pad of silica gel. The filtrate was concentrated and purified by silica gel chromatography (hexanes/EtOAc 100:0 to 70:30 gradient) to afford the title compound as a yellow solid (0.58 g, 55%). [0138] 1H NMR (500 MHz, DMSO-d6): delta 2.29 (s, 3H), 2.37 (s, 3H), 7.42 (d, J = 4.1 Hz, IH), 7.49 (d, J = 8.3 Hz, 2H), 7.55 (s, IH), 8.03 (d, J= 8.4 Hz, 2H), 8.07 (s, IH), 8.09 (d, J — 4.1 Hz, 2H) MS (ES+): m/z 404 (M+H)+

The chemical industry reduces the impact on the environment during synthesis 934524-10-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3438-46-8 ,Some common heterocyclic compound, 3438-46-8, molecular formula is C5H6N2, 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.

In a RBF, dry THF (3 mL) was added followed by DIA (0.158 mL,0.397 mL, 2.78 mmol, 4.2 equiv.). This solution was cooled to 78C and treated with n-BuLi (1.669 mL, 2.72 mmol, 4.1 equiv., 1.6 Min hexane) and stirred for 10 min. To this solution, 2-methylpyridine(0.262 mL, 247 mg, 2.65 mmol, 4 equiv.) was added dropwise.After 30 min, a solution of methyl 2-hydroxy-4-(methoxymethoxy)-6-methylbenzoate (13, 150 mg, 0.663 mmol) was addeddropwise to the pyridine solution. The yellow solution was kept at78 C and allowed to warm to rt over 2 h. The solvent wasremoved under vacuum, and dichloromethane (10 mL) was addedand washed with water (5 mL). The organic layer was dried overMgSO4 and concentrated. The residue was purified on silica (2%MeOH: DCM) to give the MOM-ether as a yellow solid.

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. 3438-46-8, 4-Methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Qian; Kulkarni, Amol A.; Sajith, Ayyiliath M.; Hussein, Dilbi; Brown, David; Guener, Osman F.; Reddy, M. Damoder; Watkins, E. Blake; Lassegue, Bernard; Griendling, Kathy K.; Bowen, J. Phillip; Bioorganic and Medicinal Chemistry; vol. 26; 5; (2018); p. 989 – 998;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 954220-98-5 , The common heterocyclic compound, 954220-98-5, name is 2,4-Dichloro-5-fluoro-6-methylpyrimidine, molecular formula is C5H3Cl2FN2, 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.

Compound 1b (0.130 g, 0.718 mmol), compound Int-1 (0.204 g, 0.718 mmol)And DIPEA (0.401 g, 2.730 mmol) were sequentially added to tetrahydrofuran (30 mL)And absolute ethanol (2 mL), heated to reflux and stirred for 12 h. Quench with water,Extract twice with ethyl acetate (30 mL), combine the ethyl acetate layers,It was washed with saturated brine (30 mL), dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure.Silica gel column chromatography (PE / EA = 20/1 to 10/1) was purified to obtain 0.115 g of pale yellow oil,That is, compound 1c.

The synthetic route of 954220-98-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yinxingshu Pharmaceutical (Suzhou) Co., Ltd.; Chen Li; Shao Qing; Gan Libin; (22 pag.)CN110590768; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia