Day: September 15, 2021

Synthetic Route of 105742-66-3, Adding some certain compound to certain chemical reactions, such as: 105742-66-3, name is 4,5-Dichloro-2,6-dimethylpyrimidine,molecular formula is C6H6Cl2N2, 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 105742-66-3.

General procedure: A mixture of intermediates 8 (5 mmol), (2-phenyloxazol-4-yl)methanamines 4 (5 mmol), and anhydrous potassium carbonate (1.4 g, 10 mmol) were taken in a 1:1 DMF:Water (20 mL) and heated at 80 C for 3-4 h. The progress of reaction was monitored by TLC. After completion of reaction, the reaction mixture was poured into saturated saline and extracted with ethyl acetate (3 x 50 mL). The combined organic layers was dried over Na2SO4 and removed under reducing pressure to give the crude product. The residue was recrystallized from the mixture of petroleum ether (50 mL) and ethyl acetate (10 mL) to give pure target compounds 9 in 79-86% yield.

According to the analysis of related databases, 105742-66-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Ning; Huang, Ming-Zhi; Liu, Ai-Ping; Liu, Min-Hua; Li, Li-Zhong; Zhou, Chun-Ge; Ren, Ye-Guo; Ou, Xiao-Ming; Long, Chu-Yun; Sun, Jiong; Dang, Ming-Ming; Lan, Zhi-Li; Chemical Papers; vol. 74; 3; (2020); p. 963 – 970;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 36082-50-5 ,Some common heterocyclic compound, 36082-50-5, molecular formula is C4HBrCl2N2, 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.

5-Bromo-2,4-dichloropyrimidine B1-a (2.28 g, 10 mmol) and 30 mL of tetrahydrofuran were sequentially added to a dry 100 mL one-necked flask, and a 2N aqueous sodium hydroxide solution (10 mL, 20 mmol) was stirred under ice-cooling. The reaction temperature was raised to room temperature and the reaction was stirred at room temperature for 6 hours. After completion of the reaction, the reaction solution was cooled to 0 C and the pH of the reaction solution was adjusted to 3-4 using a 6N hydrochloric acid solution. The mixture was extracted with chloroform (50 mL×3) and EtOAc (1.8 g, 86% yield).

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. 36082-50-5, 5-Bromo-2,4-dichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Qingyu Pharmaceutical Technology Co., Ltd.; Zou Bin; Ma Shichao; Fu Xianlei; Dong Hongping; (130 pag.)CN109942556; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4316-93-2, 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. 4316-93-2, name is 4,6-Dichloro-5-nitropyrimidine, molecular formula is C4HCl2N3O2, 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 solution of dibenzylamine (26.17g) in dichloromethane (60 mL) was added drop-wise into a solution of 4,6-dichloro-5-nitropyrimidine (20.0 g) in dichloromethane (140 mL) over an ice bath. Triethylamine (18.3 mL) was added, and the mixture was stirred for 1 hour. Water was added to the reaction mixture, the organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain the title compound (32.1 g) as a pale yellow solid.

According to the analysis of related databases, 4316-93-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUN PHARMA ADVANCED RESEARCH COMPANY LIMITED; KADIYALA, V.S.N. Murty; RAUT, Virendra Narendra; SAVANT, Pratit; SHETH, Chetana Kaushal; CHAUDHARI, Umesh Vishnu; RATHOD, Rajendrasinh Jashvantsinh; BHATT, Tushar Bhupendrabhai; CHITTURI, Trinadha Rao; (50 pag.)WO2017/134685; (2017); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 62802-42-0, 2-Chloro-5-fluoropyrimidine, 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, Recommanded Product: 2-Chloro-5-fluoropyrimidine, blongs to pyrimidines compound. Recommanded Product: 2-Chloro-5-fluoropyrimidine

To a solution of 2-chloro-5-fluoropyrimidine (10.0 g, 75.46 mmol, Sigma Aldrich) in DMF (100 mL) was added tributyl(vinyl)tin (31.1 g, 98.09 mmol) at ambient temperature. The reaction mixture was purged with N2 for 5 mm and then Pd(PPh3)4 (2.62 g, 2.26 mmol) was added. The reaction mixture was further degassed with N2 for 5 mm and then stirred at 100 C for 24 h. After completion of the reaction (m onitored by TLC), the reaction mixture was cooled to ambient temperature and quenched with water (100 mL). The aqueous layer was extracted with Et20 (2 x 100 mL) and the combined organic layers were washed with brine (100 mL), dried over anhydrous Na2504, and then concentrated in vacuo providing initial product which was purified by silica gel column chromatography (Redisep column 120 g; elution: 6% EtOAc in hexanes). This provided Example 351.1 (8.0 g, 85% yield) as an oil. 1H NMR (400 MHz, CDC13) oe 8.58 – 8.49 (m, 2H), 6.86 (dd, J = 17.4, 10.6 Hz, 1H), 6.53 (d,J= 17.3 Hz, 1H), 5.70 (d,J= 10.6 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62802-42-0, 2-Chloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 5909-24-0 ,Some common heterocyclic compound, 5909-24-0, molecular formula is C8H9ClN2O2S, 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 ethyl 4-chloro-2- (methylthio)pyrimidine-5-carboxylate (20.0 g, 86 mmol) in dichloromethane (400 mL) at -78 0C was added diisobutylaluminum hydride, 1.0 M in toluene (172 mL, 172 mmol). The reaction was allowed to warm to 0 0C over 2 h. To the reaction was added a 20% Rochelle’s (1600 mL) and diethyl ether (750 mL). The emulsion was stirred for 30 min. The organics were sequestered and the aqueous was extracted further with diethyl ether (2 x 500 mL). The combined organics were washed with water (500 mL), brine (500 mL), dried over MgSO4, and concentrated in vacuo and filtered through a plug of silica eluting with 1:1; ethyl acetate:CH2Cl2 to obtain compound 223 (9.6 g, 59% yield). 1H NMR (500 MHz, CDCl3) delta 8.55 (s, 1 H) 4.75 (d, J=5.87 Hz, 2 H) 2.58 (s, 3 H) 2.06 – 2.25 (m, J=5.14 Hz, 1 H) ppm.

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. 5909-24-0, Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; WO2009/85185; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 49844-90-8, 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 49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-chloro-2-(methylthio)pyrimidine (0.55 g, 3.42 mmol) and methyl tetrahydro-2/-/- pyran-4-carboxylate (494 mg, 3.42 mmol) in THF (5 ml.) at 30 C was added LHMDS (1 M in THF) (4.11 ml_, 4.1 1 mmol) dropwise. The reaction mixture was stirred at 30 C for 5 min then was poured into water (100 ml.) and extracted with EtOAc (2 x 200 ml_). The organic extract was washed with brine (1 x 100 ml_), dried (MgS04), filtered and solvent removed in vacuo to afford methyl 4-(2-(methylthio)pyrimidin-4-yl)tetrahydro-2/-/-pyran-4-carboxylate (915 mg, 3.24 mmol, 95% yield) as a pale yellow oil. Rt 1.74 min (HPLC acidic); m/z 269 (M+H)+ (ES+); 1H NMR (500 MHz, DMSO-d6) d 8.62 (d, J = 5.3 Hz, 1 H), 7.27 (d, J = 5.3 Hz, 1 H), 3.76-3.70 (m, 2H), 3.67 (s, 3H), 3.54-3.46 (m, 2H), 2.49 (s, 3H), 2.27-2.20 (m, 2H), 2.14-2.04 (m, 2H).

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 49844-90-8, 4-Chloro-2-(methylthio)pyrimidine.

Reference:
Patent; STEP PHARMA S.A.S.; QUDDUS, Abdul; NOVAK, Andrew; COUSIN, David; BLACKHAM, Emma; JONES, Geraint; WRIGGLESWORTH, Joseph; DUFFY, Lorna; BIRCH, Louise; GEORGE, Pascal; AHMED, Saleh; (267 pag.)WO2019/180244; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 7627-44-3, 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 7627-44-3, name is 2,4-Dichloro-5-(iodomethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of NaH (79.75 mg, 3.32 mmol) in anhydrous THF (50 mL) at 0° C. under nitrogen atmosphere was added 3-methyloxetan-3-ol (268.39 mg, 3.05 mmol). After stirring for 30 min at 0° C., the reaction mixture was transferred via cannula to a solution of INT-53 (800 mg, 2.77 mmol) in anhydrous THF (50 mL). After stirring for an additional 2 h at 0° C., NH4Cl (satd. aq) was added and the reaction was extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried over MgSO4, concentrated under reduced pressure and the resulting residue was purified by silica column chromatography eluting with a mixture of petroleum ether: ethyl acetate (1/1). INT-61 (350 mg, 51percent) was obtained as a brown solid. 1H NMR (400 MHz, CDCl3): delta 8.71 (s, 1H), 4.77-4.75 (d, J=6.8 Hz, 2H), 4.53 (s, 2H), 4.48-4.46 (d, J=7.2 Hz, 2H), 1.66 (s, 3H). MS m/z (M+H): 249.1.

According to the analysis of related databases, 7627-44-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Celgene Avilomics Research, Inc.; Alexander, Matthew David; Chuaqui, Claudio; Malona, John; McDonald, Joseph John; Ni, Yike; Niu, Deqiang; Petter, Russell C.; Singh, Juswinder; (164 pag.)US2016/75720; (2016); 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. 1044145-59-6, name is (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 1044145-59-6

To a solution of (4-chloro-2-(methylthio)pyrimidin-5-yl)methanol (1.14 g, 6 mmol) in DCM (200 mL) was added MnO2 (8.7 g, 100 mmol), the reaction was stirred at r.t. overnight, then filtered, the filtrate was concentrated to give 4-chloro-2-(methylthio)pyrimidine-5-carbaldehyde as a yellow solid , which was used for the next step without purification. Yield: 72.7%, MS (m/z): 188.9 (M+1) +.

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, 1044145-59-6, (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-guo; DAI, Guangxiu; XIAO, Kun; JIA, Hong; ZHANG, Zhulin; VENABLE, Jennifer Diane; BEMBENEK, Scott Damian; CHAI, Wenying; WO2014/15830; (2014); 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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide, the common compound, a new synthetic route is introduced below. HPLC of Formula: C5H4ClN3O

To a 5 mL vial containing a stir bar, 3-(2-aminopyrimidin-5-yl)-6-cyclobutyl-2-fluorophenol (80 mg, 0.31 mmol) and 2-chloropyrimidine (41 mg, 0.34 mmol) were added Cs2CO3 (203 mg, 0.62 mmol) and DMSO (0.8 mL). The resultant mixture was stirred at 120 Celsius for approximately 1 hour via microwave irradiation. The reaction mixture was cooled to room temperature before passing the mixture through a syringe filter and subjecting the filtrate to FCC to afford the title compound (81 mg, 78%). MS (ESI): mass calcd. for C18H16FN5O, 337.13; m/z found, 338.1 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.57 (d, J=4.8, 2H), 8.50 (d, J=1.0, 2H), 7.31-7.19 (m, 2H), 7.09-7.05 (m, 1H), 5.40 (s, 2H), 3.71 (p, J=8.9, 1H), 2.28-2.07 (m, 4H), 2.03-1.89 (m, 1H), 1.86-1.74 (m, 1H).

The synthetic route of 22536-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2014/221310; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 81560-03-4, 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 81560-03-4, name is 5-Bromo-2-(methylthio)pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Step 3, Preparation of 5-bromo-4-chloro-2-methylthiopyrimidine: take 5-bromo-2-methylthio-4-pyrimidinone 110g, dissolve in 400g pyridine, and raise the temperature of the system to 80.100 g of phosphorus oxychloride was added dropwise. After the addition was completed, the reaction was continued for 5 h. After the reaction was completed,Cool to room temperature, ice bath, adjust the pH to 8-9 with saturated sodium bicarbonate, extract with 500 ml of ethyl acetate, dry over anhydrous magnesium sulfate, filter,The filtrate was decompressed to recover the solvent, and the residue was recrystallized from petroleum ether:ethyl acetate=1:3 to obtain 98 g of light yellow solid powder in a yield of 83%.

According to the analysis of related databases, 81560-03-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Weiju Industrial Co., Ltd.; Liu Hui; (6 pag.)CN107488175; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia