Category: 22536-66-9

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 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

1.4. 2-[1-[2-(2-Methoxyphenoxy)ethyl]piperidin-4-yl-amino]pyrimidine-4-carboxamide, hydrochloride. 2.1 g (0.0073 mol) of 1-[2-(2-methoxyphenoxy)-ethyl]piperidin-4-amine, 1.15 g (0.0073 mol) of 2-chloropyrimidine-4-carboxamide and 3 g (0.0219 mol) of potassium carbonate in solution in 42 ml of N,N-dimethylformamide are introduced into a 100 ml round bottom flask. The mixture is stirred for 48 hours at room temperature, it is poured into water and then extracted three times with ethyl acetate. The organic phase is washed once with water, dried over sodium sulphate, filtered and the filtrate is concentrated under reduced pressure. The base is recrystallized from 2-propanol to give 0.7 g of base. 19 ml of a 0.1N hydrochloric acid solution in 2-propanol are added to the base in solution in a mixture of dichloromethane and 2-propanol. The solvent is evaporated under reduced pressure and the hydrochloride is recrystallized from 2-propanol. 0.26 g of compound are obtained. Melting point: 194-196 C.

With the rapid development of chemical substances, we look forward to future research findings about 22536-66-9.

Reference:
Patent; Synthelabo; US5246939; (1993); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-66-9, Adding some certain compound to certain chemical reactions, such as: 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide,molecular formula is C5H4ClN3O, 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 22536-66-9.

Methyl (2-(methylamino)ethyl)carbamic acid tert-butyl ester (1.88 g, 9.99 mmol), 2-chloropyrimidine-4-carboxamide (1.73 g, 10.98 mmol) and potassium carbonate under nitrogen. (1.52g, 10.98mmol) was added toN,N-dimethylformamide (15 mL).The reaction mixture was warmed to 130 C, stirred for 20 hr then cooled to room temperature, filtered and evaporated. The resulting residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 1/1) to afford the title compound as a white solid (2.50g, 81.0%).

According to the analysis of related databases, 22536-66-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Xu Xianjie; Zhang Yingjun; Zheng Changchun; (42 pag.)CN105085491; (2019); B;,
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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H4ClN3O

Methyl (2-(methylamino)ethyl)carbamic acid tert-butyl ester (1.88 g, 9.99 mmol), 2-chloropyrimidine-4-carboxamide (1.73 g, 10.98 mmol) and potassium carbonate under nitrogen. (1.52g, 10.98mmol) was added toN,N-dimethylformamide (15 mL).The reaction mixture was warmed to 130 C, stirred for 20 hr then cooled to room temperature, filtered and evaporated. The resulting residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 1/1) to afford the title compound as a white solid (2.50g, 81.0%).

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Xu Xianjie; Zhang Yingjun; Zheng Changchun; (42 pag.)CN105085491; (2019); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-66-9, 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.

General procedure: Aryl Halide, tetrakis (triphenylphosphine)palladium or Palladium(II) bis(triphenylphosphine) dichloride (0.05 eq) and boronic acid orpinnacol ester (1.2 eq) were weighed out into a microwave vessel or sealed tube. Acetonitrile (3 mL/mmol) and a 1M aqueous solutionof Sodium Carbonate (3 eq) were added. The vessel was capped and heatedthermally3-18 hrs at 100 C. Upon completion, the reaction was cooled and crudeproduct was either triterated via addition of water and collection byfiltration or extracted with sat ammonium chloride and DCM. If the crudeproduct was an intermediate, it was taken into the next step in most cases w/ofurther purification or alternatively submitted for reverse phase HPLCpurification when it was a final product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22536-66-9, 2-Chloropyrimidine-4-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; Blaquiere, Nicole; Castanedo, Georgette; Feng, Jianwen A.; Hu, Baihua; Staben, Steven; Yuen, Po-wai; Wu, Guosheng; Lin, Xingyu; Burch, Jason; US2015/57260; (2015); 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

Reference of 22536-66-9, 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.

To a solution of 0.07 g (0.19 mmol, 1.0 eq.) of(S)-1-amino-N-(3-chloro-4-fluorophenyl)-7- fluoro-2,3 -dihydro- 1H-indene-4-carboxami de hydrochloride (Vild) and 30 mg (0.21 mmol, 1.10 eq.) of 2-chloropyrimidine-4-carboxamide in 2 mL of NIVIP was added 0.07 ml (0.39mmol, 2.0 eq.) of N,N-diisopropylethylamine, and the mixture was subjected to microwave irradiation maintaining a reaction temperature of 130 C for 1 h. The mixture was diluted with 50 mL of ethyl acetate and washed 2 x 20 ml of water followed by 10 mL of brine. The organic phase was dried (Na2SO4), filtered and the solvent was removed in vacuo. The residue was purified by flash chromatography (Si02, eluting with a linear gradient of 0-30%ethyl acetate/hexanes) to provide 24 mg (0.05 mmol, 29%) of(S)-2-((4-((3-chloro-4- fluorophenyl)carbamoyl)-7-fluoro-2,3 -dihydro- 1H-inden- 1 -yl)amino)pyrimidine-4- carboxamide (104). LCMS: m/z found 444. 1/446.1 [M+H]. HPLC: RT = 4.13 mm (Method A); ?H NIVIR (300 MFIz, Methanol-d4) 8.50 (d, 1H), 7.93 (dd, 1H), 7.61-7.72 (m, 1H), 7.50- 7.60 (m, 1H), 7.16-7.28 (m, 2H), 7.03 (t, 1H), 5.88-5.95 (m, 1H), 3.07-3.48 (m, 2H), 2.55-2.66(m, 1H),2.10(m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22536-66-9, its application will become more common.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; COLE, Andrew, G.; DORSEY, Bruce, D.; KAKARLA, Ramesh; KULTGEN, Steven; QUINTERO, Jorge; (353 pag.)WO2018/172852; (2018); 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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

A tube containing a solution of 2-chloropyrimidine-4-carboxamide (0.24 g, 1 eq) and potassium (S)-trifluoro(3-((3-hydroxy-1-methyl-2-oxopyrrolidin-3yl)ethynyl)phenyl)borate (1 eq) in Ethanol (0.25 M) was purged with nitrogen before addition of Pd(OAc)2 (0.06 eq), RuPhos (0.12 eq), and Sodium Carbonate (2 eq). The tube was sealed and stirred at 85 C. for 18 hours. The reaction mixture was cooled to room temperature and extracted with dichloromethane and saturated ammonium chloride then dried with Magnesium sulfate, filtered and concentrated to dryness. The crude material subjected to reverse phase purification to afford 53 mg of the title compound (10%). M+H=337.0; 1H NMR (400 MHz, DMSO-d6) delta 9.16-9.11 (m, 1H), 8.70-8.60 (m, 3H), 7.98 (s, 1H), 7.94 (d, J=5.0 Hz, 1H), 7.64-7.54 (m, 2H), 6.47 (s, 1H), 3.40-3.35 (m, 2H), 2.81 (s, 3H), 2.48-2.43 (m, 1H), 2.25-2.17 (m, 1H).

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; Genentech, Inc.; Blaquiere, Nicole; Castanedo, Georgette; Feng, Jianwen A.; Hu, Baihua; Staben, Steven; Yuen, Po-wai; Wu, Guosheng; Lin, Xingyu; Burch, Jason; US2015/57260; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22536-66-9 ,Some common heterocyclic compound, 22536-66-9, molecular formula is C5H4ClN3O, 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 261 N-[10,ll-dimethyl-4-oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02’6]dodeca- l(12),6,8,10-tetraen-3-yl]-2-[(2-methoxyethyl)amino]pyrimidine-4-carboxamide (ABR 239626) To a stirred solution of 2-chloropyrimidine-4-carboxamide, available via a literature method: PCT Int. AppL, 2001068612 (330 mg, 2.08 mmol) in DMF (6 mL) was added methyl 3,3,3- trifiuoro-2-oxopropanoate (355 mu, 3.47 mmol) followed by pyridine (170 mu, 2.08 mmol) under nitrogen. The reaction was stirred at room temperature for 2 h. Thionyl chloride (150 mu, 2.08 mmol) was added at 0C. The reaction was stirred for 1 h at 0C and then concentrated. The residue was filtered through a short pad of silica, eluting with DCM, under nitrogen. The filtrate was concentrated, and the acyl intermediate that remained was dissolved in DMF (5 mL) under nitrogen. The solution of acyl intermediate was added to a solution of 5,6-dimethyl-lH-l ,3- benzodiazol-2 -amine (280 mg, 1.74 mmol) in DMF (8 mL) followed by triethylamine (280 2.08 mmol). The reaction mixture was stirred for a further 16 h and then concentrated. The residue was dissolved in EtOAc (50 mL) and washed with water (3 x 50 mL) and brine (2 x 50 mL) and then dried (MgSO_i), filtered and concentrated to afford 2-chloro-N-[10,l 1 -dimethyl-4- oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02,6]dodeca-l(12),6,8,10-tetraen-3- yl]pyrimidine-4-carboxamide. (260 mg, 15%). m/z = 424.95 (MH)+. A sealable tube was charged with a portion of 2-chloro-N-[10,l 1 -dimethyl-4-oxo-3- (trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02,6]dodeca-l(12),6,8,10-tetraen-3-yl]pyrimidine-4- carboxamide (250 mg, 0.35 mmol), 2-methoxyethan- 1 -amine (92 muL·, 1.06 mmol), K2C03 (150 mg, 1.06 mmol) and DMF (5 mL). The tube was flushed with nitrogen, sealed and stirred at 100C for 6 h. Then reaction mixture was concentrated and the resulting residue was diluted with EtOAc (20 mL) and water (20 mL). The aqueous phase was extracted with EtOAc (2 x 10 mL). The combined organic extracts were washed with 10 % citric acid (aq) (2 x 20 mL) and brine (20 mL) and then dried (MgS04), filtered and concentrated. The crude product was purified by automated reverse phase HPLC (low pH Method A) to afford the title compound as a white solid (50 mg, 31 %).

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. 22536-66-9, 2-Chloropyrimidine-4-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTIVE BIOTECH AB; WELLMAR, Ulf; LIBERG, David; EKBLAD, Maria; BAINBRIDGE, Marie; EAST, Stephen; HARGRAVE, Jonathan; PREVOST, Natacha; WO2015/177367; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-66-9 ,Some common heterocyclic compound, 22536-66-9, molecular formula is C5H4ClN3O, 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 261 N-[10,ll-dimethyl-4-oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02’6]dodeca- l(12),6,8,10-tetraen-3-yl]-2-[(2-methoxyethyl)amino]pyrimidine-4-carboxamide (ABR 239626) To a stirred solution of 2-chloropyrimidine-4-carboxamide, available via a literature method: PCT Int. AppL, 2001068612 (330 mg, 2.08 mmol) in DMF (6 mL) was added methyl 3,3,3- trifiuoro-2-oxopropanoate (355 mu, 3.47 mmol) followed by pyridine (170 mu, 2.08 mmol) under nitrogen. The reaction was stirred at room temperature for 2 h. Thionyl chloride (150 mu, 2.08 mmol) was added at 0C. The reaction was stirred for 1 h at 0C and then concentrated. The residue was filtered through a short pad of silica, eluting with DCM, under nitrogen. The filtrate was concentrated, and the acyl intermediate that remained was dissolved in DMF (5 mL) under nitrogen. The solution of acyl intermediate was added to a solution of 5,6-dimethyl-lH-l ,3- benzodiazol-2 -amine (280 mg, 1.74 mmol) in DMF (8 mL) followed by triethylamine (280 2.08 mmol). The reaction mixture was stirred for a further 16 h and then concentrated. The residue was dissolved in EtOAc (50 mL) and washed with water (3 x 50 mL) and brine (2 x 50 mL) and then dried (MgSO_i), filtered and concentrated to afford 2-chloro-N-[10,l 1 -dimethyl-4- oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02,6]dodeca-l(12),6,8,10-tetraen-3- yl]pyrimidine-4-carboxamide. (260 mg, 15%). m/z = 424.95 (MH)+. A sealable tube was charged with a portion of 2-chloro-N-[10,l 1 -dimethyl-4-oxo-3- (trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02,6]dodeca-l(12),6,8,10-tetraen-3-yl]pyrimidine-4- carboxamide (250 mg, 0.35 mmol), 2-methoxyethan- 1 -amine (92 muL·, 1.06 mmol), K2C03 (150 mg, 1.06 mmol) and DMF (5 mL). The tube was flushed with nitrogen, sealed and stirred at 100C for 6 h. Then reaction mixture was concentrated and the resulting residue was diluted with EtOAc (20 mL) and water (20 mL). The aqueous phase was extracted with EtOAc (2 x 10 mL). The combined organic extracts were washed with 10 % citric acid (aq) (2 x 20 mL) and brine (20 mL) and then dried (MgS04), filtered and concentrated. The crude product was purified by automated reverse phase HPLC (low pH Method A) to afford the title compound as a white solid (50 mg, 31 %).

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. 22536-66-9, 2-Chloropyrimidine-4-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTIVE BIOTECH AB; WELLMAR, Ulf; LIBERG, David; EKBLAD, Maria; BAINBRIDGE, Marie; EAST, Stephen; HARGRAVE, Jonathan; PREVOST, Natacha; WO2015/177367; (2015); 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. 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