Category: 4316-97-6

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;,
Pyrimidine | C4H4N2 – PubChem,
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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.Application In Synthesis of 4,6-Dichloro-5-methylpyrimidine

Preparation of 5-(6-Chloro-5-methylpyrimidin-4-yl)-1 -methyl-1 ,4,5,6- tetrahvdropyrrolor3,4-clpyrazole1-Methyl-1 ,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole bis-hydrochloride salt (2.00 g, 10.2 mmol) and 4,6-dichloro-5-methylpyrimidine (1 .66 g, 10.2 mmol) were suspended in tetrahydrofuran (51 ml.) at room temperature. To this was added triethylamine (4.41 ml_, 31.6 mmol), which caused cloudiness in the mixture and led to a brown solid sticking to the flask walls. This mixture was stirred at room temperature for 4 hours and then heated 50 degrees Celsius for an additional 19 hours. The reaction mixture was cooled to room temperature and diluted with water (100 ml_). This mixture was extracted with ethyl acetate (3 x 100 ml_). The organic extracts were pooled, washed with brine, dried over sodium sulfate, and filtered. The filtrate was reduced to dryness under vacuum to yield the title compound as a light brown solid (1.95 g, 78%), which was used in the next step without further purification. 1 H NMR (500 MHz, deuterochloroform) delta 2.54 (s, 3 H) 3.88 (s, 3 H) 4.90 (app. d, J=3.66 Hz, 4 H) 7.28 (s, 1 H) 8.29 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4316-97-6, 4,6-Dichloro-5-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton; WO2011/61679; (2011); 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., Quality Control of 4,6-Dichloro-5-methylpyrimidine

Tert-butyl 4-hydroxypiperidine-1-carboxylate (2.47 g, 12.3 mmol) and potassium tert-butoxide (1.42 g, 12.7 mmol) were added to a THF (20 mL) solution of 2,4-dichloro-3-methylpyrimidine (1.60 g, 9.82 mmol), and the mixture was stirred for 2 hours. To the reaction solution, water was added, followed by extraction with ethyl acetate three times. The obtained organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20-60:40, V/V) to obtain the title compound as colorless oil (3.07 g, yield: 95%). 1H-NMR (400 MHz, CDCl3) delta ppm: 8.39 (1H, s), 5.36-5.31 (1H, m), 3.75-3.69 (2H, m), 3.75-3.69 (2H, m), 3.39-3.33 (2H, m), 2.23 (3H, s), 2.02-1.95 (2H, m), 1.80-1.72 (2H, m), 1.48 (9H, 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; Daiichi Sankyo Company, Limited; EP2210886; (2010); A1;,
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

Reference of 4316-97-6, 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 4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of te/t-butyl-(3,4-cis)-3-fluoro-4-hydroxy-piperidine-1 -carboxylate (racemic) (1.0 g, 4.6 mmol) and 4,6-dichloro-5-methylpyrimidine (818 mg, 5.02 mmol) in anhydrous tetrahydrofuran (23 ml.) was added sodium hydride (201 mg, 5.02 mmol, 60% dispersion in mineral oil) in two portions at 0 degrees Celsius. After 18 hours, the reaction mixture was quenched with saturated aqueous ammonium chloride and diluted with water. The resulting mixture was extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to afford the title compound as a pale yellow oil (1.56 g, 99%). 1H NMR (400 MHz, deuterochloroform) delta 1.46 (s, 9 H), 1.84 – 1.91 (m, 1 H), 2.04 – 2.17 (m, 1 H), 2.24 (s, 3 H), 3.09 – 3.22 (m, 1 H), 3.29 – 3.43 (m, 1 H), 3.78 – 4.01 (m, 1 H), 4.09 – 4.20 (m, 1 H), 4.74 – 4.93 (m, 1 H), 5.31 – 5.43 (m, 1 H), 8.36 (s, 1 H). LCMS: (ES+): 346.4 (M+1 ).

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

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

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 4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H4Cl2N2

tert-Butyl (3R.4S 4-r(6-chloro i–5-methylpyrimidin-4-yl)oxyl-3- fluoropiperidine-1 -carboxylate (racemic)To a solution of ie -butyl-(3,4-cis)-3-fluoro-4-hydroxy-piperidine-1 -carboxylate(racemic) (Preparation 1 ) (1.0 g, 4.6 mmol) and 4,6-dichloro-5-methylpyrimidine (818 mg, 5.02 mmol) in anhydrous tetrahydrofuran (23 mL) was added sodium hydride (201 mg, 5.02 mmol, 60% dispersion in mineral oil) in two portions at 0 degrees Celsius. After 18 hours, the reaction mixture was quenched with saturatedaqueous ammonium chloride and diluted with water. The resulting mixture was extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to afford the title compound as a pale yellow oil (1.56 g, 99%). 1 H NMR (400 MHz, deuterochloroform) delta 1 .46 (s, 9 H), 1.84 – 1 .91 (m, 1 H), 2.04 – 2.17 (m, 1 H), 2.24 (s, 3 H), 3.09 – 3.22 (m, 1 H), 3.29 – 3.43 (m, 1 H), 3.78 – 4.01 (m, 1 H), 4.09 – 4.20 (m, 1 H), 4.74 – 4.93 (m, 1 H), 5.31 – 5.43 (m, 1 H), 8.36 (s, 1 H). LCMS: (ES+): 346.4 (M+1 ).

With the rapid development of chemical substances, we look forward to future research findings about 4316-97-6.

Reference:
Patent; PFIZER INC.; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton; WO2011/61679; (2011); 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. 4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine, molecular formula is C5H4Cl2N2, 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 4,6-Dichloro-5-methylpyrimidine

A mixture of 4,6-dichloro-5-methylpyrimidine (available from Sigma-Aldrich No.595446) (5 g, 30.70 mmol) in ammonia (7 M solution in MeOH, 15 ml, 105 mmol) was left under stirring for 40 min in a sealed vial at 140 0C. Water (300 ml) and EtOAc (600 ml) were added to the resulting white suspension and the two layers were separated. The aqueous phase was extracted with EtOAc (3 x 600 ml). The collected organic phases were dried (Na2SO4), filtered and concentrated under reduced pressure to give the title compound D3 (3.10 g, 20.73 mmol, 68% yield) as a white solid. UPLC: rt = 0.41 min, peaks observed: 144 (M+l, 100%) and 146 (M+ 1, 33%). C5H6ClN3 requires 143. 1H NMR (400 MHz, DMSO- d6) delta(ppm): 8.06 (s, 1 H), 7.09 (bs, 2 H), 2.07 (s, 3 H).

With the rapid development of chemical substances, we look forward to future research findings about 4316-97-6.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/3997; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route 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.

[00434] Step 2: Synthesis of 4,6-dichloro-2-(5-methoxy-2-(trifluoromethyl)phenyl)-5- methylpyrimidine. To a solution of 2-bromo-4-methoxy-1-(trifluoromethyl)benzene (5.0 g, 19.6 mmol) in dry THF (50 mL) stirred at -78 C under nitrogen atmosphere, was added n- Butyl lithium (8.9 mL, 2.4 M in hexane, 21.4 mmol) over a period of 5 minutes, the mixture was stirred for another 10 minutes at the same temperature before 4,6-dichloro-5- methylpyrimidine (4.5 g, 27.9 mmol) in THF (5 mL) was added slowly over 5 minutes. The resulting mixture was stirred at -78 C for 30 minutes, then quenched with HOAc (1.5 mL) and warmed to 0 C slowly. DDQ (6.6 g, 29.1 mmol) was then added portion wise and the resulting mixture was stirred at 0 C for 30 minutes, diluted with CH2Cl2(100 mL), washed with 10% NaOH (50 mL x 2) and brine (100 mL); the organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified silica column chromatography with (petroleum ether/EtOAc = 100/1 to 30/1) to render 4,6-dichloro-2-(5-methoxy-2- (trifluoromethyl) phenyl)-5-methylpyrimidine (1.0 g, 21% yield). ESI-LCMS (m/z): 337.0 [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,4316-97-6, its application will become more common.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; MORADEI, Oscar, Miguel; SHAPIRO, Gideon; JIN, Lei; BABINE, Robert, E.; (495 pag.)WO2016/44641; (2016); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature 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.

4,6-dichloro-5-methylpyrimidine (0.60g, 3.68mmol) and (3R, 4R) -1- benzyl -N, 4- dimethyl-piperidin-3-amine (0.80g, 3.68 mmol) were dissolved DMF (5mL), was added potassium carbonate (1.02g, 7.36mmol), 70 reaction was stirred overnight under nitrogen.Water was added (100 mL) to quench the reaction, extracted with ethyl acetate (70mL ¡Á 3), the organic phase water (50mL) washed with saturated aqueous sodium chloride solution (50 mL), dried the organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, performed column chromatography (eluent: PE / EtOAc (v / v) = 1/1), to give the product 1.08g, yield: 85.0%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4316-97-6, 4,6-Dichloro-5-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Liu, Bing; Huang, Jiuzhong; Ren, Xingye; Li, Zhi; Zhang, Yingjun; Zhang, Changchun; (55 pag.)CN105566321; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia