Month: March 2022

Synthetic Route of 163263-91-0, 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 163263-91-0 as follows.

To a solution of 2,4-dichloro-6-(4-methoxyphenyl)pyrimidine (1.01 g, 3.96 mmol) and (+/-)-trans-methyl 3 -aminobicyclo[2 .2. 2]octane-2-carboxylate (871 mg, 4.75 mmol) in N,N-dimethylformamide (20 mL) was added potassium carbonate (0.81 g, 5.88mmol). The mixture was stirred at rt overnight. To the reaction mixture was added water (70 mL), and the mixture was extracted with EtOAc (100 mL x 3). The combined organic layers were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to dry.The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a white solid (1.01 g, 64%).MS-ESI: (ESI, pos.ion) m/z: 402.2 [M+Hfb;?H NIVIR (400 IVIFIz, CDC13) (ppm): 7.98 (d, J = 8.7 Hz, 2H), 6.98 (d, J = 8.9 Hz, 2H), 6.72 (s, 1H), 5.46 (d, J= 6.3 Hz, 1H), 4.32 (s, 1H), 3.88 (s, 4H), 3.74 (s, 3H), 2.39 (d, J= 5.1 Hz, 1H),2.08 (s, 1H), 1.90-1.84 (m, 1H), 1.78-1.56 (m, 8H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,163263-91-0, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; REN, Qingyun; TANG, Changhua; YIN, Junjun; YI, Kai; ZHANG, Yingjun; (264 pag.)WO2018/33082; (2018); 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. 37482-64-7, name is 2-Chloro-4-ethoxy-6-methylpyrimidine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H9ClN2O

To a round bottom flask containing 600 mg (3.48 mmol) of 39, 489 mg (5.22 mmol) of azetidine hydrochloride, 131 mg (0.69 mmol) of Cul, 164 mg (0.69 mmol) of 3,4,7,8-tetramethyl- 1,10-phenanthroline and 2.83 g (8.70 mmol) of Cs2CO3 was added 15 mL of dry degassed DMF. The reaction mixture was stirred at 50 C for 3 h. The mixture was allowed to cool to room temperature and then filtered through Celite and the Celite pad was washed with CH2C12. The combined organic phase was washed with water and then with brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (15 x 3 cm). Elution with 19:1 hexane-EtOAc followed by 9:1 hexane-EtOAc afforded 40 as a colorless solid:yield 565 mg (84%); mp 42-43 C; silica gel TLC Rf 0.29 (3:2 hexane-EtOAc); ?H NMR (CDC13, 400 MHz) 8 1.24 (t, 3H,J 7.2 Hz), 2.16 (s, 3H), 2.20 (quint, 2H,J 7.6 Hz), 4.01 (t, 4H,J 7.6 Hz), 4.20 (q, 2H,J= 7.2 Hz) and 5.73 (s, 1H); ?3C NMR (CDC13, 100 MHz) 6 14.4, 16.1,23.9,49.9,61.2, 95.0, 163.0, 167.7 and 170.1; mass spectrum (APCI), rn/z 194.1289 (M+H) (C,0H,6N30 requires 194.1293).

The synthetic route of 37482-64-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY; HECHT, Sidney; KHDOUR, Omar; ALAM, Mohammad; DEY, Sriloy; CHEN, Yana; CHEVALIER, Arnaud; (90 pag.)WO2016/133959; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1254710-16-1, 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. 1254710-16-1, name is 8-Bromo-7-chloro-2-phenyl-[1,2,4]triazolo[1,5-c]pyrimidine. A new synthetic method of this compound is introduced below.

General procedure: A mixture of 5a (0.16 g, 0.5 mmol), the appropriate amine (1.5mmol, 3.0 equiv), and Et3N (0.51 g, 5 mmol) in anhydrous MeOH(15 mL) was stirred under reflux for 24 h until full consumption ofthe substrates. The progress of the reaction was monitored by TLC(eluent: PE-EtOAc, 3:1). Then, the mixture was concentrated underreduced pressure. The residue was directly subjected to columnchromatography on silica gel using PE-EtOAc (8:1) as the eluent toafford, respectively, the desired 7,8-bis(amino)-substituted[1,2,4]triazolo[1,5-c]pyrimidines 6g and 6h.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1254710-16-1, 8-Bromo-7-chloro-2-phenyl-[1,2,4]triazolo[1,5-c]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Tang, Caifei; Wang, Chao; Li, Zhiming; Wang, Quanrui; Synthesis; vol. 46; 20; (2014); p. 2734 – 2746;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 60186-89-2, 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 60186-89-2 as follows.

To a suspension of 4-bromo-2,6-dimethoxypyrimidine (Intermediate A) (10.3 g, 46.8 mmol) and sodium hydrogen carbonate (NaHCCh) (5.51 g, 65.6 mmol) in MeOH/H20 (1 : 1, 120 mL) at room temperature was added bromine (4.34 mL, 84.2 mmol). The reaction mixture was stirred at room temperature for 1.5 hours. The mixture was diluted with dichloromethane (DCM) (100 mL) and the layers were separated. The aqueous phase was extracted with DCM (2 x 30 mL). The organic extracts were combined, filtered through a phase separator cartridge and concentrated in vacuo. The crude product was purified by chromatography on silica gel (220 g, 0-10% EtOAc in isohexane, gradient elution) to afford the title compound 4,5-dibromo-2,6-dimethoxypyrimidine (8.48 g, 60%) as a pale orange solid. Analytical data: Rl 2.24 min (Method 1); m/z 297/299/301 (M+H)+ (ES+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60186-89-2, its application will become more common.

Reference:
Patent; CORCEPT THERAPEUTICS INCORPORATED; HUNT, Hazel; CREPIN, Damien Francis Philippe; HILL-COUSINS, Joseph Thomas; BAKER, Thomas Matthew; DUFFY, Lorna; (0 pag.)WO2019/236487; (2019); 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. 4214-85-1, name is 2-Amino-6-methyl-5-nitro-3H-pyrimidin-4-one, molecular formula is C5H6N4O3, 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. COA of Formula: C5H6N4O3

A suspension of 2-amino-6-methyl-5-nitropyrimidin-4-one (G. N. Mitchell et. al. J. Org. Chem . , 1974, 39, 176) (20.0 g) in acetic anhydride (120 ML) was heated under reflux for 0.5 h.. The cooled suspension was filtered and the solids washed with ether to give 2-N-acetyl-6-methyl-5-nitropyrimidin-4-one (19.7 g).. 13C NMR (d6-DMSO) delta 174.5, 161.9, 153.3, 150.9, 133.8, 24.2, 21.4.

With the rapid development of chemical substances, we look forward to future research findings about 4214-85-1.

Reference:
Patent; Industrial Research Limited; Albert Einstein College of Medicine of Yesheva University; US6693193; (2004); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 19808-30-1, 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. 19808-30-1, name is 5-Bromopyrimidin-4(3H)-one. A new synthetic method of this compound is introduced below.

Step 3: 5-Bromo-4-chloropyrimidine[0362] Into a 500-mL round-bottomed flask was charged with 5- bromopyrimidin-4-ol (22 g, 63.22 mmol, 1.00 equiv, 50 %), N,N- dimethylbenzenamine (4 mL), POCI3 (266.8 g). The resulting solution was stirred at 1300C in an oil bath overnight. The mixture was cooled down to room temperature and diluted with ether (1 L). The pH was adjusted to 9 with sodium bicarbonate/water. The resulting mixture was extracted with ether (4×1 L). Combined organic layers were washed with brine (2×1 L), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum affording 5-bromo-4- chloropyrimidine as black liquid (15 g, 124%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,19808-30-1, 5-Bromopyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; KALYPSYS, INC.; KAHRAMAN, Mehmet; SMITH, Nicholas, D.; BONNEFOUS, Celine; NOBLE, Stewart, A.; PAYNE, Joseph, E.; WO2010/88518; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1480-66-6, 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.1480-66-6, name is 6-Chloro-2-(trifluoromethyl)pyrimidin-4-amine, molecular formula is C5H3ClF3N3, molecular weight is 197.5456, as common compound, the synthetic route is as follows.

General procedure: To a solution of 6-chloro-2-methylpyrimidin-4-amine (1.0 equiv.) in THF (0.17M) was added BOC2O (1.1 equiv.) and DMAP (cat.). The reaction was allowed to stir overnight, then concentrated to a yellow crude, and filtered through a pad of SiO2 eluting with EtOAc and hexanes (1:1) to afford an off-white solid (78 %).

Statistics shows that 1480-66-6 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-2-(trifluoromethyl)pyrimidin-4-amine.

Reference:
Article; Nishiguchi, Gisele A.; Burger, Matthew T.; Han, Wooseok; Lan, Jiong; Atallah, Gordana; Tamez, Victoriano; Lindvall, Mika; Bellamacina, Cornelia; Garcia, Pablo; Feucht, Paul; Zavorotinskaya, Tatiana; Dai, Yumin; Wong, Kent; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2328 – 2332;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3438-61-7, 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. 3438-61-7, name is 5-Amino-4-methylpyrimidine, molecular formula is C5H7N3, 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.

5-benzyloxymethyl– isoxazole-3-carboxylic acid (0.24g, 1.0mmol), 5- amino-4-methylpyrimidine (0.13g, 1.2mmol), 1- hydroxybenzotriazole (0.01 g, 0.1mmol) was added to the chloroform (amylene addition of goods) (2.5mL). To the mixture, it was added at room temperature 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.24 g, 1.2 mmol), and stirred for 3 hours at 50 C.. Then, water was added to the reaction mixture, and the mixture was extracted twice with chloroform. After removing impurities through the organic layer to a short column which was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, represented by the following formula N-(4- methyl-pyrimidin-5-yl) -5-benzyloxymethyl – isoxazole-3-carboxamide (hereinafter, the present invention compound (39) referred to.) was obtained 0.16g.

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 3438-61-7, 5-Amino-4-methylpyrimidine.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; MITSUDERA, HIROMASA; OKAJIMA, MAYUMI; AWASAGUCHI, KENICHIRO; UJIHARA, KAZUYA; (111 pag.)JP2016/30727; (2016); 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. 1250967-81-7, name is 2-Chloro-4-isopropoxypyrimidine. A new synthetic method of this compound is introduced below., name: 2-Chloro-4-isopropoxypyrimidine

A mixture of (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (5 mg, 8 pmol), 18F (15 mg, 0.04 mmol) ,2-chloro-4-isopropoxypyrimidine (8 mg, 0.05 mmol), BINAP (5 mg, 8 pmol), Pd2(dba)3 (2 mg, 4 pmol) and Cs2C03 (20 mg, 0.06 mmol) in toluene (1 mL) was heated in a sealed tube to 110 C overnight, then was cooled to RT and concentrated in vacuo. The residue was dissolved in THF (0.5 mL), MeOH (0.5 mL), and H20 (0.5 mL). LiOH.H20 (17 mg, 0.4 mmol) was added and the reaction was stirred at RT for 14 h, then was concentrated in vacuo. The residue was taken up in EtOAc (2 mL)/H20 (1 mL), and the solution was adjusted to pH ~ 5 with IN aq. HC1. The mixture was extracted with EtOAc (3 x 2 mL); the combined organic extracts were dried (MgS04) and concentrated in vacuo. The residue was dissolved in DMF and purified via preparative LC/MS: Column: XBridge Cl 8, 200 mm x 19 mm, 5-pm particles; Mobile Phase A: 5:95 MeCN:H20 with 0.1% TFA; Mobile Phase B: 95:5 MeCN:H20 with 0.1% TFA; Gradient: a 0-min hold at 18% B, 18-58% B over 20 min, then a 4-min hold at 100% B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fractions containing the desired product were combined and dried via centrifugal evaporation to afford the title compound (bis-TFA salt, 1 mg, 3% yield; 84% purity by LC-MS). LCMS, [M + H]+ = 468.4. NMR (500 MHz, DMSO-de) d 8.31 (s, 1H), 8.08 (d, J= 5.7 Hz, 1H), 7.92 (s, 1H), 6.18 (d, J= 5.7 Hz, 1H), 5.10 – 4.98 (m, 1H), 4.75 (s, 1H), 3.72 (s, 3H), 2.68 – 2.59 (m, 1H), 2.27 (s, 3H), 2.01 – 1.47 (m, 8H), 1.21 – 1.15 (m, 6H). hLPAi IC50 = 1014 nM.

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, 1250967-81-7, 2-Chloro-4-isopropoxypyrimidine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; WANG, Ying; CHENG, Peter Tai Wah; LI, Jun; WALKER, Steven J.; (147 pag.)WO2019/126089; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 30561-07-0, Adding some certain compound to certain chemical reactions, such as: 30561-07-0, name is 2,4-Dimethoxy-5-nitropyrimidine,molecular formula is C6H7N3O4, 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 30561-07-0.

To a QianCap glass reactor (1850 mL) equipped with magnetic stirrer was added C-7A2 (100 g, 540 mmol) followed by THF (800 mL). Next, 10 % palladium on carbon (2 g) was added in one portion and the reactor was connected to the source of the hydrogen. Hydrogen pressure was set at 2 bar and reaction was well stirred for 16 h under continuous flow of hydrogen. After that time, UPLCMS analysis has shown complete conversion of starting material. The reaction mixture was filtered through the Cellite pad and the filtrate was concentrated in vacuo to around 150 – 200 mL. Then, n-hexane (500 mL) was added dropwise and the suspension was stirred for 2 h at room temperature. The precipitate was filtered, washed twice with n-hexane (2 x 50 mL) and vacuum dried. As a result, amine C-7A was obtained as a yellow/green solid (77.94 g, 93 % yeld, 99 % purity according to UPLCMS analysis).

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. 30561-07-0, 2,4-Dimethoxy-5-nitropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Adamed sp. z o.o.; FEDER, Marcin; MAZUR, Maria; KALINOWSKA, Iwona; JASZCZEWSKA, Joanna; LEWANDOWSKI, Wojciech; WITKOWSKI, Jakub; JELEN, Sabina; WOS-LATOSI, Katarzyna; (56 pag.)EP3511334; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia