Day: August 16, 2021

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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. A new synthetic method of this compound is introduced below., Product Details of 22536-66-9

2.4. 2-[1-[2-(4-Fluorophenoxy)ethyl]piperidin-4-ylamino]-pyrimidine-4-carboxamide, hydrochloride. 5.5 g (0.02 mol) of 1-[2-(4-fluorophenoxy)ethyl]-piperidin-4-amine, 3.15 g (0.02 mol) of 2-chloropyrimidine-4-carboxamide, 6.91 g (0.05 mol) of potassium carbonate and 0.4 g of sodium iodide are suspended, under argon, in 40 ml of N,N-dimethylformamide. The mixture is stirred at room temperature for 17 hours and then at 40-45 C. for 8 hours. The mixture is cooled to room temperature, poured into 150 ml of water and extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. After chromatography on silica (eluent: dichloromethane/methanol 97.5/2.5 to 90/10), 4.95 g of base are obtained. The hydrochloride is prepared from it by reaction with a 0.1N hydrochloric acid solution in 2-propanol. After recrystallisation from ethanol, 4.1 g of compound are obtained. Melting point: 202-205 C.

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, 22536-66-9, 2-Chloropyrimidine-4-carboxamide.

Reference:
Patent; Synthelabo; US5246939; (1993); A;,
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. 2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine. A new synthetic method of this compound is introduced below., Safety of 2,4-Dichloro-5-fluoropyrimidine

To a solution of 2,4-dichloro-5-fluoropyrimidine (1 .02 g, 6.08 mmol) inTHF/NMP (38 mL/3 ml_) was added Fe(acac)3 (215 mg, 0.61 mmol) and the mixture was cooled to 0 oC. 3.0 M methylmagnesium bromide in Et2O (3.04 ml_, 9.12 mmol) was added dropwise. After 30 min at 0 oC, the reaction was complete and quenched with saturated aqueous NH CI solution. Et2O was added and the layers were separated and the aqueous layer was further extracted with several portions of Et2O. The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (Hexanes to 10% EtOAc/Hexanes) gave the desired product as a waxy white solid (430 mg, 48%). 1H NMR (400 MHz, CDCI3): 8.35 (s, 1 H), 2.55 (d, J = 2.5 Hz, 3H).

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, 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHAI, Wenying; LETAVIC, Michael, A.; LY, Kiev, S.; PIPPEL, Daniel, J.; RUDOLPH, Dale, A.; SAPPEY, Kathleen, C.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; SOYODE-JOHNSON, Akinola; STOCKING, Emily, M.; SWANSON, Devin, M.; WO2011/50198; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 289042-12-2 , The common heterocyclic compound, 289042-12-2, name is tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate, molecular formula is C29H40FN3O6S, 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 4 (3R,5S,6E)-7-[4-(4-Fluorophenyl)-2-[Methyl(Methylsulfonyl)Amino]-6-(Propan-2-Yl)Pyrimidin-5-Yl]-3,5-Dihydroxyhept-6-Enoic Acid-2-Methylpropan-2-Amine (1:1) Hydrochloric acid (2 N; 60 mL) was added to a solution of tert-butyl [(4R,65)-6-{(E)-2-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]ethenyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate (Example 3; 50 g) in acetonitrile (500 mL) at room temperature and stirred at the same temperature for 3 hours. After completion of the reaction, aqueous solution of sodium hydroxide (10%; 90 mL) was added to the reaction mixture at room temperature and the temperature of the mixture was allowed to rise to 40 C. to 45 C. The pH of the reaction mixture was adjusted to 12 to 12.8 using aqueous solution of sodium hydroxide (10%). Acetonitrile was recovered completely under vacuum at 45 C. to 50 C. De-ionized water (250 mL) was added to the resulting residue at room temperature. Methyl tert-butyl ether (200 mL) was added to the mixture and stirred for 10 minutes. Layers were separated and methyl tert-butyl ether (200 mL) was added to the aqueous layer and stirred for 10 minutes. Layers were separated and aqueous layer was cooled to 5 C. to 10 C. and adjusted to a pH of 3.5 to 4.0 using hydrochloric acid (2N). Dichloromethane was added to the resulting mixture and stirred for 10 minutes to 15 minutes. Dichloromethane was recovered completely under vacuum at 35 C. to 40 C. Acetonitrile (500 mL) was added to the resulting residue and mixture was cooled to 0 C. to 5 C. To this cooled layer, tert-butyl amine (7 g) was slowly added for 30 minutes at 0 C. to 5 C. and stirred for 2 hours at 10 C. to 15 C. The product was filtered, washed with acetonitrile (50 mL) and dried under vacuum at 45 C. for 3 hours. Dry weight: 40 g

The synthetic route of 289042-12-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; Pandya, Vishwesh Pravinchandra; Richhariya, Santosh; Divya, Prabhakar; Meeran, Hashim Nizar Poovanathil Nagoor; Tewari, Neera; US2013/150579; (2013); A1;,
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 24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H5ClN4

General procedure: A mixture of 4 (50 mg; 0.296 mmol), Na2CO3 (60.74 mg; 0.592 mmol), Pd(PPh3)4 (34.66 mg; 0.030 mmol) and boronic acid (1.5 equiv.) was heated at 130 C in dioxane/water (4/1, 3 mL) for 3h. The reaction was followed by TLC. After completion, the mixture was filtered by celite and concentrated under vacuum. The solid obtained was submitted to a column chromatography. The increase of polarity in solvent gradient was made from neat petroleum ether to mixture of AcOEt/petroleum ether (6:4).

With the rapid development of chemical substances, we look forward to future research findings about 24415-66-5.

Reference:
Article; Loubidi, Mohammed; Moutardier, Anais; Campos, Joana F.; Berteina-Raboin, Sabine; Tetrahedron Letters; vol. 59; 11; (2018); p. 1050 – 1054;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 941685-26-3 ,Some common heterocyclic compound, 941685-26-3, molecular formula is C12H18ClN3OSi, 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.

A mixture of intermediate 2 (3 g, 10.6 mmol), 1-butanol (30 mL)3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1- (triisopropylsilyl) -1H-pyrrole (4.5 g, 12.7 mmol),Water (30 mL) and potassium carbonate (3.7 g, 26.5 mmol) was stirred at 100 & lt; 0 & gt; C.Then, tetrakis (triphenylphosphine) palladium (0) (0.7 g, 0.53 mmol) was added to the solution,The mixture was stirred at 100 & lt; 0 & gt; C overnight.After cooling to room temperature,The mixture was filtered through a bed of celite,Extraction under reduced pressure,Purification by silica gel column gave Intermediate 8 (2 g, 60%),As a yellow oil;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,941685-26-3, its application will become more common.

Reference:
Patent; Hangzhou East China Pharmaceutical Group New Drug Institute Co., Ltd.; Yin Jianming; Lv Yubin; Li Bangliang; (18 pag.)CN106905322; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 20090-58-8 ,Some common heterocyclic compound, 20090-58-8, molecular formula is C5H6ClN3, 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.

4-chloro-5-methylpyrimidin-2-amine (100 mg, 0.697 mmol), 1- (methylsulfonyl)piperazine (458 mg, 2,79 mmol) and potassium carbonate (289 mg, 2.090 mmol) were suspended in DMA (2322 m.) and heated to 105 C for 16 h. After cooling to rt, the reaction mixture was decanted into EtOAc and H20. The aqueous phase was extracted with EtOAc (2x). The combined organic layers were washed with 10% Li Cl solution, dried over MgSOr and concentrated to a amber oil which was dried under vacuum to afford the titled compound (134 mg, 71%). 1H NMR (400 MHz, DMSO-d6) d 7.74 (s, 1H), 6.02 (s, 2H), 3.44 – 3.35 (m, 4H), 3.25 – 3.17 (m, 4H), 2.91 (s, 3H), 2.03 (s, 3H); LC/MS | M H i 272.1; LC RT 0 48 min (Column: BEH C18 2 1 x 50mm; Mobile Phase A: water with 0.05% TFA; Mobile Phase B: acetonitrile with 0.05% TFA; Temperature: 50 C; Gradient: 2-98% B over 1.7 min; Flow: 0.8 mL/min).

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. 20090-58-8, 4-Chloro-5-methylpyrimidin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; TARBY, Christine M.; NORRIS, Derek J.; LO, Julian C.; AHUJA, Vijay T.; SEITZ, Steven P.; GAVAI, Ashvinikumar V.; TOKARSKI, John S.; RAJASAGI, Mohini; WICHROSKI, Michael; BROEKEMA, Matthias; (155 pag.)WO2019/213340; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90905-33-2, 2-Methylpyrimidine-5-carbaldehyde, 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, name: 2-Methylpyrimidine-5-carbaldehyde, blongs to pyrimidines compound. name: 2-Methylpyrimidine-5-carbaldehyde

Step-2: 2-Methyl-pyrimidine-5-carbaldehvde oxime:To a mixture of 2-methyl-5-formyl-pyrimidine (180 gm) and hydroxylamine hydrochloride (128 gm) in 50percent v/v aqueous methanol (3600 ml) was added sodium carbonate (94 gm). The reaction mixture was stirred at 30°C for 0.5 h. The resulting suspension was cooled and filtered at -10°C to provide single isomer of title compound in 1 13.5 gm quantity (56percent) as a solid.H’NMR: (DMSO-de) delta 1 1.64 (s, 1H), 8.83 (s, 2H), 8.14 (s, 1H), 2.60 (s, 3H).Further processing of the filtrate such as evaporation and salt removal, provided a mixture of isomers in 51 gm quantity which can be used for the next reaction.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90905-33-2, 2-Methylpyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; WOCKHARDT LIMITED; TRIVEDI, Bharat; DESHPANDE, Prasad; TADIPARTHI, Ravikumar; GUPTA, Sunil; DIWAKAR, Santosh; PAWAR, Shivaji; PATIL, Vijay; DEKHANE, Deepak; PATEL, Mahesh; BHAVSAR, Satish; MISHRA, Amit; SOLANKI, Manish; JAFRI, Mohammad; BHAGWAT, Sachin; WO2012/76989; (2012); 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. 4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine. A new synthetic method of this compound is introduced below., COA of Formula: C5H4Cl2N2

(1) The compound produced by the method of the Reference Example 15 (6.2g, 38mmol) was dissolved in THF (100ml), followed by addition of 2,4-difluorophenylboronic acid (7.2g, 45.6mmol), tetrakis(triphenylphosphine)palladium (2.3g, 2mmol), potassium carbonate (12.6g, 91.3mmol) and water (30ml), and the mixture was refluxed under heating for 4 hours. 2,4-Difluorophenylboronic acid (2.4g, 15mmol) and tetrakistriphenylphosphine palladium (0.8g, 0.7mmol) were additionally added, and the mixture was refluxed under heating for 2 hours. The reaction mixture was concentrated, and water was added to the residue, followed by extraction with chloroform. The extract was washed with water, dried and concentrated by evaporationg the solvent. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 5:1) to obtain 4-chloro-6-(2,4-difluorophenyl)-5-methylpyrimidine (4.6g, oil). 1H-NMR(CDCl3) delta 2.30(3H, s), 6.90-7.10(2H, m), 7.43-7.52(1H, m), 8.89(1H, s)

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, 4316-97-6, 4,6-Dichloro-5-methylpyrimidine.

Reference:
Patent; Sumitomo Chemical Takeda Agro Company, Limited; EP1333029; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 26452-81-3, 4-Chloro-6-methoxypyrimidine, 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, 26452-81-3, blongs to pyrimidines compound. name: 4-Chloro-6-methoxypyrimidine

B) 6-methoxypyrimidine-4-carbonitrile To a solution of 4-chloro-6-methoxypyrimidine (10.6 g) in acetonitrile (150 mL) was added 1,4-diazabicyclo[2.2.2]octane (8.18 g), and the mixture was stirred at room temperature for 10 min. Tetraethylammonium cyanide (11.5 g) was added to the obtained reaction mixture, and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.00 g) as a pale-yellow oil. 1H NMR (300 MHz, DMSO-d6) delta 4.00 (3H, s), 7.75 (1H, s), 8.96 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26452-81-3, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIWATASHI, Seiji; SUZUKI, Hideo; OKAWA, Tomohiro; MIYAMOTO, Yasufumi; YAMASAKI, Takeshi; HITOMI, Yuko; HIRATA, Yasuhiro; EP2816032; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 39906-04-2, Adding some certain compound to certain chemical reactions, such as: 39906-04-2, name is 4,6-Dichloro-2-methylpyrimidin-5-amine,molecular formula is C5H5Cl2N3, 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 39906-04-2.

A microwave vial was charged with 5-amino-4,6-dichloro-2-methyl-pyrimidine (4) (700 mg, 3.91 mmol), 4-methoxybenzylamine (510 ml, 3.91 mmol), and K2CO3 (810 mg,5.86 mmol) in anhydrous DMF (10 mL). The vessel was sealed and irradiated at 150 C for 1 h. After cooling, dichloromethane was added (20 mL) and the crude reaction mixture was washed with saturated aqueous NH4Cl (15 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by flash chromatography (dichloromethane:methanol 20:1) to yield 696 mg (64%) of 11 as a yellow solid. Mp 155-157 C. MS (ES, positive mode):m/z 279 (M+H)+ with a Cl isotopic pattern. 1H NMR (DMSO-d6, 300 MHz) delta: 2.52 (s, 3H, CH3-2), 2.68 (s, 3H, CH3-8), 3.71(s, 3H, OCH3), 5.39 (s, 2H, CH2), 6.89 (d, 2H, J=8.6 Hz, Ar), 7.17 (d,2H, J=8.5 Hz, Ar).

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. 39906-04-2, 4,6-Dichloro-2-methylpyrimidin-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Canela, Mara-Dolores; Liekens, Sandra; Camarasa, Mara-Jos; Priego, Eva Mara; Prez-Prez, Mara-Jess; European Journal of Medicinal Chemistry; vol. 87; (2014); p. 421 – 428;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia