58347-49-2 | Pyrimidines

09/22/21 News Share a compound : 58347-49-2

The synthetic route of 58347-49-2 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 58347-49-2, 7-Chloropyrazolo[1,5-a]pyrimidine, 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, Safety of 7-Chloropyrazolo[1,5-a]pyrimidine, blongs to pyrimidines compound. Safety of 7-Chloropyrazolo[1,5-a]pyrimidine

EXAMPLE 18N-r(35r)-l-{7-Fluoro-8-methyl-3-r(15r)-l-(pyrazolorL5-alphalpyrimidin-7-ylamino>;)ethyl1- quinolin-2-vUpyrrolidin-3-yl]cyclopropanecarboxamide(5)-(-)-3 -Amino- 1-pyrrolidinecarboxylic acid tert-butyl ester (500 mg, 2.68 mmol), DCM (30 mL), DIPEA (2 mL) and cyclopropanecarbonyl chloride (0.275 mL, 3 mmol) were combined at r.t. under a nitrogen atmosphere. The reaction mixture was stirred for 1 day, then diluted with DCM (50 mL) and washed with water (50 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo to give a brown oil. This oil, MeOH (10 mL) and 2N HCl in Et2O (5 mL) were stirred at r.t. for 3 days. The reaction mixture was then concentrated in vacuo. The resulting material, Intermediate 15 (500 mg, 1.48 mmol), H-BuOH (16 mL) and DIPEA (2 mL) were combined in a sealed tube and heated to 13O0C for 15 days. The reaction mixture was cooled, concentrated onto silica and purified by column chromatography (SiO2, 0-100% EtOAc in isohexane) to give a tan solid. This material, MeOH (10 mL) and 2N HCl in Et2O (7 mL) were combined and stirred at r.t. for 24 h. The reaction mixture was concentrated to give a brown glass. A portion of this material (50 mg, 0.127 mmol), n- BuOH (6 mL), DIPEA (1 mL) and 7-chloropyrazolo[l,5-alpha]pyrimidine (50 mg, 0.25 mmol) were combined in a sealed tube and heated under microwave irradiation to 16O0C for 2 h. The reaction mixture was then concentrated to dryness and purified by preparative HPLC to give the title compound (32.3 mg, 54%) as a brown glass. 6H (DMSO-d6) 8.44 (IH, d, J6.91 Hz), 8.38 (IH, d, J6.91 Hz), 8.25 (IH, s), 8.17 (IH, d, J 2.27 Hz), 8.10 (IH, d, J5.21 Hz), 7.57 (IH, dd, J8.84, 6.41 Hz), 7.10 (IH, t, J9.10 Hz), 6.49 (IH, d, J2.27 Hz), 6.06 (IH, d, J 5.28 Hz), 5.27 (IH, m), 4.50-4.42 (IH, m), 4.07- 3.94 (2H, m), 3.82-3.74 (IH, m), 3.60 (IH, dd, J 10.47, 5.21 Hz), 2.51 (3H, s), 2.32-2.23 (IH, m), 2.04-1.94 (IH, m), 1.77 (3H, d, J6.54 Hz), 1.66-1.58 (IH, m), 0.77-0.67 (4H, m). LCMS (ES+) 474 (M+H)+, RT 2.51 minutes {Method I).

The synthetic route of 58347-49-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BROWN, Julien, Alistair; BUeRLI, Roland; HAUGHAN, Alan, Findlay; LANGHAM, Barry, John; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2010/133836; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The origin of a common compound about 7-Chloropyrazolo[1,5-a]pyrimidine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58347-49-2, its application will become more common.

Electric Literature of 58347-49-2, 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. 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below.

A solution of 7-chloropyrazolo[i,5-ajpyrimidine (0.1 g, 0.651 mmol), 6- bromo-3-fluoro-2-methylpyridine (0.124 g, 0.651 mmol) and 1,1,1,2,2,2- hexamethyldistannane (0.213 g, 0.651 mmol) in 1,4-dioxane (2 mL) was purged withnitrogen gas for 10 mm. Pd(Ph3P)4 (0.075 g, 0.065 mmol) was added to the reaction mixture and the solution was purged with nitrogen gas again for 10 mm. The reaction mixture was heated in a microwave at 150C for 2 h. The reaction mixture was concentrated and the residue obtained was dissolved in ethyl acetate (20 mL) and water (20 mL). The biphasic mixture was filtered through diatomaceous earth (Diatomaceous earth) and the bed was washed with ethyl acetate (25 mL). The ethyl acetate layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford a brown colored solid. The solid was purified by silica gelchromatography (0-40% EtOAc in pet ether) to afford 7-(5-fluoro-6-methylpyridin-3- yl)pyrazolo[1,5-ajpyrimidine (0.06 g, 0.263 mmol, 40% yield) as a light yellow solid. LCMS (ESI) m/e 228.22 [(M+H), calcd for C12H9FN4 229.2j; LC/MS retention time (Method Al): tR = 2.20 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58347-49-2, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Share a compound : 7-Chloropyrazolo[1,5-a]pyrimidine

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, 58347-49-2, 7-Chloropyrazolo[1,5-a]pyrimidine.

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. 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below., Formula: C6H4ClN3

EXAMPLE 584-{7-Fluoro-8-methyl-3-r(l»S^-l-(pyrazolori,5-alpha1pyrimidin-7-ylamino’)ethyl]quinolin-2- yl I piperazine- 1 -carboxamide Intermediate 36 (50 mg, 0.151 mmol), 7-chloropyrazolo[l,5-alpha]pyrimidine (34.7 mg, 0.226 mmol), DIPEA (0.079 mL, 0.453 mmol) and n-BuOH (1 mL) were combined and heated under microwave irradiation at 1400C for 1 h. After cooling, the mixture was dissolved in EtOAc (100 mL) and washed with saturated brine (3 x 20 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. Purification by preparative HPLC gave the title compound (7 mg, 10%) as a yellow solid. deltaH (DMSO-d6) 8.24 (d, J4.99 Hz, IH), 8.14 (s, IH), 8.10 (d, J2.33 Hz, IH), 7.70 (dd, J8.89, 6.22 Hz, IH), 7.25 (t, J9.13 Hz, IH), 6.58 (d, J7.55 Hz, IH), 6.51 (d, J2.33 Hz, IH), 6.40 (d, J 5.03 Hz, IH), 5.46 (s, 2H), 5.05 (t, J6.89 Hz, IH), 3.95-4.02 (m, 2H), 3.81-3.88 (m, 2H), 3.67-3.75 (m, 2H), 3.27-3.32 (m, 2H), 2.49 (d, J2.33 Hz, 3H), 1.29 (d, J6.59 Hz, 3H). LCMS (ES+) 449 (M+H)+, RT 2.59 minutes (Method 2).

Extended knowledge of 58347-49-2

According to the analysis of related databases, 58347-49-2, the application of this compound in the production field has become more and more popular.

Synthetic Route of 58347-49-2, Adding some certain compound to certain chemical reactions, such as: 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine,molecular formula is C6H4ClN3, 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 58347-49-2.

A solution of 7-chloropyrazolo[l,5-ajpyrimidine (0.1 g, 0.651 mmol), 6-bromo-2-(difluoromethyl)-3 -fluoropyridine (0.162 g, 0.716 mmol) and 1,1,1,2,2,2-hexamethyldistannane (0.235 g, 0.7 16 mmol) in 1,4-dioxane (2 mL) was purged with nitrogen gas for 10 mi Pd(Ph3P)4 (0.075 g, 0.065 mmol) was added to the reaction mixture and the solution was purged with nitrogen gas for another 10 mm. The reaction mixture was heated at 150 C for 1.5 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue waspurified by silica-gel chromatography (pet ether/ethyl acetate (0-40%)) to afford 7- (6-(difluoromethyl)-5-fluoropyridin-2-yl) pyrazolo [1,5-al pyrimidine (40 mg, 0.151 mmol, 23% yield) as a yellow solid .LCMS (ESI) m/e 265.0 [(M+H), calcd for C12H8F3N4 265.11; LC/MS retention time (Method Al): tR = 2.08 mm.

According to the analysis of related databases, 58347-49-2, the application of this compound in the production field has become more and more popular.

The origin of a common compound about 7-Chloropyrazolo[1,5-a]pyrimidine

According to the analysis of related databases, 58347-49-2, the application of this compound in the production field has become more and more popular.

Electric Literature of 58347-49-2, 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 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 15Ethyl (4- { 8 -chloro-3 – IY 1 S)- 1 -(pyrazolof 1 ,5 -a]pyrimidin-7-ylamino)ethyllquinolin-2- yl } piperazin- 1 – vDacetateIntermediate 22 (500 mg, 1.05 mmol), EtOH (5 mL) and 2N HCl in Et2O (5 mL) were combined and stirred at r.t. for 4 days. The reaction mixture was then concentrated to give a yellow glass (526 mg, quantitative). A portion of this material (50 mg, 0.11 mmol), «-BuOH (6 mL), DIPEA (1 mL) and 7-chloropyrazolo[l,5-alpha]pyrimidine (50 mg, 0.25 mmol) were combined in a sealed tube and heated under microwave irradiation to 14O0C for 1 h. The reaction mixture was then concentrated and purified by preparative HPLC to give the title compound (39.3 mg, 72%) as a tan glass. deltaH (DMSOd6) 8.68 (IH, s), 8.47 (IH, d, J7.70 Hz), 8.14-8.09 (2H, m), 7.86-7.76 (2H, m), 7.40 (IH, t, J7.81 Hz), 6.44 (IH, d, J2.27 Hz), 6.26 (IH, d, J5.28 Hz), 5.14-5.05 (IH, m), 4.16 (2H, q, J7.10 Hz), 3.47-3.38 (2H, m), 3.42 (2H, s), 3.38-3.29 (2H, m), 3.00-2.93 (2H, m), 2.90-2.82 (2H, m), 1.90 (3H, d, J 6.69 Hz), 1.25 (3H, t, J 7.09 Hz). LCMS (ES+) 494/496 (M+H)+, RT 3.50 minutes {Method 1).

According to the analysis of related databases, 58347-49-2, the application of this compound in the production field has become more and more popular.

A new synthetic route of 7-Chloropyrazolo[1,5-a]pyrimidine

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 58347-49-2, 7-Chloropyrazolo[1,5-a]pyrimidine.

Electric Literature of 58347-49-2, 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. 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine, molecular formula is C6H4ClN3, 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.

EXAMPLE 1 Preparation of 7-(3,5-di-t-butyl-4-hydroxyphenyl)-aminopyrazolo[1,5-a]pyrimidine: A suspension of 7-chloropyrazolo[1,5-a]pyrimidine (1.0 g), 3,5-di-t-butyl-4-hydroxyaniline hydrochloride (1.8 g) and diethylaniline (2.3 ml) in toluene (50 ml) is heated at 120 C. for 30 minutes. After cooling, the solvent is distilled off, and the residue is purified by silica gel column chromatography (solvent; CHCl3) to give 7-(3,5-di-t-butyl-4-hydroxyphenyl)aminopyrazolo[1,5-a]pyrimidine (890 mg) as colorless crystal. M.p. 264-266 C. (decomposed) 1 H-NMR (CDCl3): delta 1.48 (s, 18H), 5.63 (s, 1H), 5.92 (s, 1H), 6.55 (d, J=2.3 Hz, 1H), 7.47 (s, 2H), 8.14 (d, J=2.3 Hz, 1H)

Reference:
Patent; Otsuka Pharmaceutical Factory, Inc.; US5688949; (1997); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Share a compound : 58347-49-2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58347-49-2, its application will become more common.

Electric Literature of 58347-49-2, 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 58347-49-2 as follows.

EXAMPLE 242-rDimethylaminoVl-(4-{7-fluoro-8-methyl-3-r(lS)-l-rpyrazolori.5-alpha1pyrimidin-7- ylamino)ethyl1quinolin-2-vUpiperazin- 1 -vDethanone Intermediate 15 (700 mg, 2.06 mmol), 2-(dimethylamino)-l-(piperazin-l-yl)- ethanone (500 mg), ?-BuOH (10 mL) and DIPEA (2 mL) were combined in a sealed tube and heated to 13O0C for 13 days. The reaction mixture was cooled, concentrated onto silica and purified by column chromatography (SiO2, 0-10% MeOH in EtOAc) to give a white solid. This material, MeOH (8 mL) and 2N HCl in Et2O (4 mL) were combined and stirred at r.t. for 2 days. The reaction mixture was concentrated to give a yellow foam. A portion of this material (50 mg, 0.12 mmol), n-BuOH (6 mL), DIPEA (1 mL) and 7-chloropyrazolo[l,5-alpha]pyrimidine (50 mg, 0.25 mmol) were combined in a sealed tube and heated to 13O0C for 16 h. The reaction mixture was then concentrated to dryness and purified by preparative HPLC to give the title compound (28 mg, 48%) as a tan glass. deltaH (DMSO-Ci6) 8.64 (IH, s), 8.41 (IH, d, J7.80 Hz), 8.13 (2H, m), 7.74 (IH, dd, J8.95, 6.28 Hz), 7.33 (IH, t, J9.13 Hz), 6.44 (IH, d, J2.27 Hz), 6.28 (IH, d, J5.30 Hz), 5.21- 5.13 (IH, m), 4.16-3.73 (4H, m), 3.42-3.17 (6H, m), 2.56 (3H, s), 2.25 (6H, s), 1.89 (3H, d, J 6.71 Hz). LCMS (ES+) 491 (M+H)+, RT 3.23 minutes {Method 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58347-49-2, its application will become more common.

Sources of common compounds: 58347-49-2

A solution of 7-chloropyrazolo[l,5-ajpyrimidine (0.1 g, 0.651 mmol), 5- bromo-2-fluoronicotinonitrile (prepared as described in Example 487) (0.131 g, 0.651 mmol) and 1,1,1,2,2,2-hexamethyldistannane (0.213 g, 0.651 mmol) in 1,4- dioxane (2 mL) was purged with nitrogen gas forlO mm. Pd (Ph3P)4 (0.075 g, 0.065mmol) was added to the reaction mixture and the solution was purged with nitrogen gas again for 10 mm. The reaction mixture was heated in a microwave at 150 C forh. The reaction mixture was concentrated and the residue obtained was dissolved in ethyl acetate (20 mL) and water (20 mL). The biphasic mixture was filtered through diatomaceous earth (Diatomaceous earth) and the bed was washed withethyl acetate (25 mL). The ethyl acetate layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford a brown colored solid. The solid was purified by silica gel chromatography (0-40% EtOAc in pet ether) to afford 2-fluoro-5 -(pyrazolo [1,5 -aj pyrimidin-7-yl)nicotinonitrile (0.032 g, 0.134 mmol, 21% yield) as a light-yellow color solid. LCMS (ESI) m/e 239.0 [(M), calcdfor C12H6FN5 239.11; LC/MS retention time (Method Al): tR = 2.33 mm.

Analyzing the synthesis route of 7-Chloropyrazolo[1,5-a]pyrimidine

With the rapid development of chemical substances, we look forward to future research findings about 58347-49-2.

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. 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine, molecular formula is C6H4ClN3, 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: 58347-49-2

EXAMPLE 46(S)-A- { 5,7-Difluoro-3 -[ 1 -(pyrazolof 1 ,5 -alpha]pyrimidin-7-ylamino)ethyllquinolin-2-yl} – piperazin-2-oneA solution of Intermediate 30 (61.2 mg, 0.20 mmol), 7-chloropyrazolo[l,5-alpha]- pyrimidine (33.8 mg, 0.2 mmol) and DIPEA (28.5 mg, 0.22 mmol) in M-BuOH (3 mL) was heated at 12O0C for 16 h. The solvent was removed in vacuo and the residue purified by preparative HPLC to afford the title compound (14.9 mg, 18%) as a cream solid. 6H (CDCl3) 8.45 (IH, s), 8.13 (IH, d, J5.2 Hz), 8.02 (IH, s), 7.35 (IH, dd, J 8.8 Hz), 6.90 (IH, t, J8.8 Hz), 6.88 (IH, d, J6.4 Hz), 6.55 (IH, br s), 6.48 (IH, s), 5.89 (IH, d, J5.2 Hz), 5.12-5.18 (IH, m), 4.09 (2H, q, J 17.5 Hz), 3.52-3.68 (4H, m), 1.88 (3H, d, J6.8 Hz). LCMS (ES+) 424 (M+H)+, RT 3.07 minutes {Method 1).

With the rapid development of chemical substances, we look forward to future research findings about 58347-49-2.

Extended knowledge of Formula: C6H4ClN3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58347-49-2, its application will become more common.

Adding a certain compound to certain chemical reactions, such as: 58347-49-2, 7-Chloropyrazolo[1,5-a]pyrimidine, 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, 58347-49-2, blongs to pyrimidines compound. Formula: C6H4ClN3

A solution of 7-chloropyrazolo[1,5-ajpyrimidine (0.05 g, 0.326 mmol), (8)-tert-butyl (1 -(2-chloro-4-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate (prepared as described in Example 260, Part A and B) (0.152 g, 0.326 mmol), C52CO3 (0.212 g, 0.65 1 mmol), and KBr (0.039 g, 0.326 mmol) in 1,4-dioxane (10 mL) and water (1 mL) was purged with nitrogen gas for 30 mi PdC12 (dppf)-CH2C12 adduct (0.027 g, 0.033 mmol) was added to the reactionmixture and the solution was purged with nitrogen gas again for 10 mm. The reaction mixture was heated at 80 C for 12 h. The reaction mixture was concentrated and the residue obtained was dissolved in ethyl acetate (30 mL) and water (30 mL). The biphasic mixture was filtered through diatomaceous earth. The diatomaceous earth was washed with ethyl acetate (50 mL). The organic layer wasseparated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford cmde product as a brown solid which was purified by silica-gel column chromatography (pet ether/ethyl acetate) to afford (5)-tert-butyl (1 -(2-chloro-4- (pyrazolo [1,5 -aj pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate (0.08 g, 0.174 mmol, 54% yield) as an off-white solid. LCMS (ESI) m/e 459.2 [(M+H) ,calcd for C24H32C1N403 459.21; LC/MS retention time (Method Al): tR = 3.28 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58347-49-2, its application will become more common.