Tag: M.W:100-200

Synthetic Route of 3167-50-8 ,Some common heterocyclic compound, 3167-50-8, molecular formula is C5H5N3O2, 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.

General procedure: A solution of 2-(2-methyl-1H-indol-1-yl)ethanamine (4a) (65 mg, 0.373 mmol) and 4-(piperidin-1-yl)benzoic acid (5) (76 mg, 1 eq.), and dimethylaminopyridine (catalytic, ?5 mg) in dichloromethane (6 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide.hydrochloride (EDCI) (92 mg, 1.3 eq.) at room temperature. The resulting reaction mixture was stirred for 6h. At the conclusion of the reaction (TLC), water (15 mL) was added to quench the reaction. The product was extracted with ethyl acetate (20mL×3). Organics were washed with dilute HCl (10 mL), saturated NaHCO3 solution (10 mL), water (10 mL) and brine solution (10 mL) and dried over Na2SO4 and concentrated. The resulting crude product was subjected to silica gel chromatography eluting with 0-40% ethyl acetate in hexane to furnish 7k (TG7-152) (100mg, 74% yield). 1H NMR (CDCl3): delta 7.52 (d, J=5.6Hz, 1H), 7.49 (d, J=8.8Hz, 2H), 7.30 (d, J=8Hz, 1H), 7.07 (m, 2H), 6.80 (d, J=8.2Hz, 2H), 6.23 (s, 1H), 5.98 (t, J=5.4Hz, 1H), 4.33 (t, J=6Hz, 2H), 3.76 (q, J=6Hz, 2H), 3.25 (t, J=4.8Hz, 4H), 2.37 (s, 3H), 1.6 (m, 6H). LCMS (ESI): >97% purity at lambda 254, MS; m/z, 362 [M+H]+. Anal. Calcd. for C23H27N3O: C, 76.42; H, 7.53; N, 11.62; found; C, 76.48; H, 7.55; N, 11.59.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3167-50-8, its application will become more common.

Reference:
Article; Ganesh, Thota; Jiang, Jianxiong; Dingledine, Ray; European Journal of Medicinal Chemistry; vol. 82; (2014); p. 521 – 535;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 6345-43-3, Adding some certain compound to certain chemical reactions, such as: 6345-43-3, name is Dimethyl pyrimidine-4,6-dicarboxylate,molecular formula is C8H8N2O4, 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 6345-43-3.

General procedure: A solution of the corresponding dimethyl ester (10mmol) and hydrazine hydrate (10.9mL, 11.2g, 220mmol) in ethanol (150mL) was heated under reflux for 18h and then cooled to room temperature. The precipitate was filtered, washed twice with ethanol, once with ether, and dried, to give the bis(acylhydrazide) which was sufficiently pure and employed without further purification.

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. 6345-43-3, Dimethyl pyrimidine-4,6-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Reznichenko, Oksana; Quillevere, Alicia; Martins, Rodrigo Prado; Loaec, Nadege; Kang, Hang; Lista, Maria Jose; Beauvineau, Claire; Gonzalez-Garcia, Jorge; Guillot, Regis; Voisset, Cecile; Daskalogianni, Chrysoula; Fahraeus, Robin; Teulade-Fichou, Marie-Paule; Blondel, Marc; Granzhan, Anton; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 13 – 29;,
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Pyrimidine – Wikipedia

Application of 10320-42-0, 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. 10320-42-0, name is 2-Chloro-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

Dodecylmercaptan (24.77 mL) was dissolved in DMF (150 mL) and cooled to 0°C,60percent NaH (4.14 g) was added and stirred for 10 minutes, and2-chloro-5-nitropyrimidine (15 g) was added to the mixture, which was then stirred for1 hour at 0°C. Water was added to the reaction solution, and the resulting solid waswashed with water to obtain the object compound (26.01 g).NMR2: 0.88(3H, t, J=7.OHz), 1.18-1.38(16H, m), 1.38-1.50(2H, m), 1.64-1.76(2H, m),3.23(2H, t, =7.5Hz), 9.23(2H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10320-42-0, 2-Chloro-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; SHINOHARA, Tomoichi; IWATA, Shin; ARAI, Kenta; ITO, Nobuaki; SUZUKI, Masaki; (53 pag.)WO2018/221667; (2018); A1;,
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Application of 851984-15-1 , The common heterocyclic compound, 851984-15-1, name is 6-Chloro-5-fluoropyrimidin-4-amine, molecular formula is C4H3ClFN3, 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 the Boc protected amine 31.15 (1 eq) was in 1 ,4-dioxane (50 eq) was added HC1 (4 N in 1 ,4 dioxane 15 eq) and the solution was heated to 60 oC for 60 min. The solvent was removed in vacuo and the crude amine (1.0 eq) was dissolved in 1 -butanol (100 eq) and treated with 6-chloro-5-fluoropyrimidin-4- amine (1.5 eq) and DIPEA (10.0 eq). The reaction solution was stirred at 1 10 C for 16 h, cooled to rt and diluted with EtOAc (20 mL), washed with H20 (10 mL), saturated brine (10 mL), dried ( a2S04), filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (Petroleum ether/EtOAc 1/1) to give the desired product compound 279 as light yellow solid (63% yield).1.. NMR (400 MHz, CDC13) delta 7.93 (br. s., 1H), 6.44 (br. s., 1H), 6.39 (br. s., 1H), 6.23 (br. s., 1H), 4.71 (m, 1H), 4.01 (m, 1H), 3.82 (m, 1H), 3.40 (br. s., 1H), 3.17 – 3.23 (m, 1), 2.47 (br. s., 1H), 2.35 (s, 2H), 2.35 (m, 1H), 2.03 (br. s., 2H), 1.60 (br. s., 1H). EIMS (m/z): calcd. for C2oH22ClF3 60 (M+) 454.8, found 454.8.

The synthetic route of 851984-15-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN IDEC MA INC.; ERLANSON, Daniel, A.; MARCOTTE, Doug; KUMARAVEL, Gnanasambandam; FAN, Junfa; WANG, Deping; CUERVO, Julio, H.; SILVIAN, Laura; POWELL, Noel; BUI, Minna; HOPKINS, Brian, T.; TAVERAS, Art; GUAN, Bing; CONLON, Patrick; ZHONG, Min; JENKINS, Tracy, J.; SCOTT, Daniel; SUNESIS PHARMACEUTICALS, INC.; LUGOVSKOY, Alexey, A.; WO2011/29046; (2011); 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. 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, the common compound, a new synthetic route is introduced below. Safety of 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde

4,6-Dichloropyrimidine-5-acetaldehyde 1 (2.0 g, 10.5 mmol) dissolved in 80 mLEthanol, adding triethylamine (3.0 mL,21.06 mmol), stirred at room temperature for 10 min.Then tert-butylamine (2.2 mL, 21.06 mmol) was added to the mixture, and the reaction solution wasAfter stirring at 90 C for 6 h, the reaction was monitored by TLC. After the reaction is completed, after evaporating the solvent,The crude reaction product was dissolved in dichloromethane/water.(volume ratio = 1:1) 100 ml × 3 times.Separation and purification by column chromatography to obtain a white solid1.0 g (yield 55.2%).

The synthetic route of 16019-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University Huaxi Hospital; He Yang; Chai Yingying; Li Weimin; Zhou Xinglong; (20 pag.)CN108794483; (2018); A;,
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Pyrimidine – Wikipedia

Related Products of 4316-97-6, 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.

1 -(6-Chloro-5-methylpyrimidin-4-yl)-2,3-dihvdro-1 H-imidazon ,2- blpyrazoleTo a solution of 2,3-dihydro-1 H-imidazo[1 ,2-b]pyrazole (Preparation 12) (14.1 g, 129 mmol) and 4,6-dichloro-5-methylpyrimidine (21.1 g, 129 mmol) in 800 mL of tetrahydrofuran cooled down to zero degrees Celsius was added sodium bis(trimethylsilyl)amide (1 M in tetrahydrofuran, 138 ml_, 138 mmol) drop-wise over 1 hour. After 2 hours, water was added and tetrahydrofuran evaporated. Dichloromethane was then added and the aqueous phase was extracted 3 times with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was dissolved in a minimum amount of dichloromethane and the desired product was precipitated using heptane. The resulting solid was filtered, washed with heptane and dried under vacuum to give 24.6g (90% yield) of a beige solid. LCMS (ES+): 236.3 (M+1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4316-97-6, its application will become more common.

Reference:
Patent; PFIZER INC.; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton; WO2011/61679; (2011); A1;,
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Electric Literature of 4316-97-6 ,Some common heterocyclic compound, 4316-97-6, molecular formula is C5H4Cl2N2, 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.

4,6-dichloro-5-methylpyrimidine (0.98 g, 6.0 mmol), 4-chloro-2-methylphenylboronic acid (2.24 g, 13 . 2 mmol), acetonitrile (100 ml) and 1 M sodium carbonate (Na 2 CO 3) (30 ml), and nitrogen bubbling was carried out for 1 hour.Thereafter, 2210 mg of PdCl 2 (PPh 3), 0.3 mmol) was added and the reaction was carried out under reflux. The reaction solution was a yellow clear solution. Disappearance of the raw material was confirmed by TLC after 3 hours.After a while, since an orange solid precipitated, suction filtration was carried out, after washing with methanol, the filtrate was dissolved in chloroform. Washed with water 150 ml × 3 times, brine 150 ml × 1 time, and evaporation was carried out. In order to remove the catalyst, silica gel column chromatography was carried out. A glass filter 17G-4 was used and 150 cc of silica gel was used.The injection solvent was toluene, and the developing solvent was hexane: ethyl acetate = 10: 3 (vol / vol). After the evaporation, 1.0 g of a white solid was obtained, and the yield was 49%. From 1 H-NMR and MS, it was confirmed that 3 MHPM-Cl (molecular weight 343) was formed.

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; YAMAGATA UNIVERSITY; SASABE, HISAHIRO; KIDO, JUNJI; KOMATSU, RYUTARO; NAKAO, KOHEI; (58 pag.)JP2018/35129; (2018); A;,
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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. 1005-38-5, name is 4-Amino-6-chloro-2-(methylthio)pyrimidine, molecular formula is C5H6ClN3S, 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. Quality Control of 4-Amino-6-chloro-2-(methylthio)pyrimidine

EXAMPLE 124 3-[4-(3,5-Dichloropyrid-4-ylcarboxamido)phenyl]-2-[4-chloro-2-(methylthio)pyrimidin-6-yl amino]propanoic acid 6-Amino-4-chloro-2-(methylthio)pyrimidine gave the title compound (1.4mg) HPLC-MS Retention time 2.63 min; MH+ 512.

With the rapid development of chemical substances, we look forward to future research findings about 1005-38-5.

Reference:
Patent; Celltech Therapeutics Limited; US6348463; (2002); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3177-24-0, 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 3177-24-0 as follows.

To a cooled (-60 °C) solution of (lr,4r)-4-ethoxycyclohexanamine (6.82 g, 37.9 mmol) and 2,4-dichloropyrimidine-5-carbonitrile (6 g, 34.5 mmol) in THF (115 mL) was added DIEA (15.02 mL, 86 mmol) dropwise. The resulting mixture was stirred at -60 °C for 1 h and then allowed to warm to room temperature overnight. The resulting mixture was concentrated and the residue was purified by silica gel column- 125 -ATI-2514175vl chromatography (14 percent ethyl acetate in petroleum ether). The product fractions were combined and concentrated to afford 2-chloro-4-((lr,4r)-4-ethoxycyclohexylamino)- pyrimidine-5-carbonitrile (3.33 g, 11.86 mmol, 34.4 percent yield) and 4-chloro-2-((lr,4r)-4- ethoxycyclohexylamino)pyrimidine-5-carbonitrile (5.5 g, 19.59 mmol, 56.8 percent yield;1H NMR (400 MHz, DMSO-d6) delta ppm 8.62 – 8.87 (m, 2 H), 3.61 – 3.86 (m, 1 H), 3.44 (dd, J=7.03, 2.34 Hz, 2 H), 3.12 – 3.26 (m, 1 H), 1.75 – 2.15 (m, 4 H), 1.13 – 1.44 (m, 4 H), 1.08 (td, J=6.93, 1.76 Hz, 3 H); MS (ESI) m/z 281.1 [M+l]+) as white solids. Theregiochemistry of the major isomer was confirmed by comparison with the proton spectra of 4-chloro-2-((lr,4r)-4-methoxycyclohexylamino)pyrimidine-5-carbonitrile (synthesis described herein).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3177-24-0, its application will become more common.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); 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. 22536-63-6, name is 2-Chloro-4-methoxypyrimidine, molecular formula is C5H5ClN2O, 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. Recommanded Product: 22536-63-6

2-Bromopyridine or 2-chloropyrimidine (2equiv.), 5-amino-2-substitutedphenol (lequiv) and 37% HCl solution (2equiv) in 10% aqueous EtOH solution (0.2M) was stirred at 9O0C for 24h. The reaction mixture was diluted with AcOEt and washed with 5% aqueous K2CO3 solution and brine. The organic phase was dried over Na2SO4, concentrated and the crude product was purified by flash chromatography on silica gel.; Following the general procedure for the synthesis of 2-R-5-(heteroaryl-2-ylamino)phenol, 2- chloro-4-methoxypyrimidine (44 mg, 0.30 mmol) and 4-amino-o-cresol (37 mg, 0.30 mmol) in 10% aqueous EtOH (2 mL) was heated at 90 0C for 18h. The title compound was obtained in 21 % yield a (14 mg) and used for the next step without addittional purification. 1H NMR (500 MHz, CD3OD) £8.06 (d, J= 5.8 Hz, IH), 7.25 (d, J= 2.0 Hz, IH), 6.98 (d, J = 8.2 Hz, IH), 6.92 (dd, J= 8.2, 2.0 Hz, IH), 6.18 (d, J= 5.8 Hz, IH), 3.97 (s, 3H), 2.16 (s, 3H); 13C NMR (125 MHz, CD3OD) £ 172.1, 162.1, 159.1, 156.8, 140.3, 131.9, 120.2, 112.9, 108.5, 99.8, 54.5, 16.1.

With the rapid development of chemical substances, we look forward to future research findings about 22536-63-6.

Reference:
Patent; YALE UNIVERSITY; WO2007/38387; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia