Category: 705263-10-1

Reference of 705263-10-1, Adding some certain compound to certain chemical reactions, such as: 705263-10-1, name is 6-Bromopyrazolo[1,5-a]pyrimidine,molecular formula is C6H4BrN3, 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 705263-10-1.

The intermediate of formula VI (30 mmOl, 5.9 g)And the substance of formula VII (30 mmol, 4.6 g)Was placed in a 250 ml round bottom flask equipped with a reflux condenser, potassium carbonate (90 mmol, 12.4 g) and Pd (PPh3) 4 (3 mmol, 3.3 g) were added, dioxane (90 ml) and water (30 ml ), Stirred under nitrogen for three times, heated under nitrogen to 110 C, stirred for 4 h,After completion of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The mixture was extracted with 100 ml of water and 100 ml of dichloromethane. The organic phase was separated and the aqueous phase was extracted with dichloromethane 50 ml chi 3 for 3 times. Dried over sodium sulfate, the solvent was removed by suction filtration, and the residue was purified by column chromatography with ethyl acetate / petroleum ether to give 5.5 g of a pale yellow product.The pale yellow product is an intermediate of formula III-1,The yield of the intermediate of formula III-1 was calculated to be 82%.

According to the analysis of related databases, 705263-10-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Zhipulai Bio-pharmaceutical Technology Co., Ltd.; Chen Wei; Zhao Gang; Pu Lin; Liu Jifeng; (13 pag.)CN105130991; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 705263-10-1 ,Some common heterocyclic compound, 705263-10-1, molecular formula is C6H4BrN3, 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 of 6-bromopyrazolo[1,5-a]pyrimidine (S2, 1 equiv) in DMF/H2O (9:1, 10 vol) was added compound S1 (1 equiv), K2CO3(2 equiv), and tetrakis(triphenylphosphine)palladium (0.1 equiv). The reaction mixture was stirred at 90 C. for 5 h and then concentrated. The remaining residue was purified by column chromatography on silica gel to give compound S3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,705263-10-1, its application will become more common.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 705263-10-1, 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. 705263-10-1, name is 6-Bromopyrazolo[1,5-a]pyrimidine, molecular formula is C6H4BrN3, 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.

In a muwave vial, 6-bromopyrazolo[1,5-a]pyrimidine, 9, (0.25 g, 1.26 mmol, 1.0 eq), 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine, 10, (0.36 g, 1.26 mmol, 1.0 eq), and Pd(dppf)Cl2?DCM (52.0 mg, 0.06 mmol, 0.05 eq) were added. The muwave vial was evacuated under reduced pressure and purged with Argon (3x). To the mixture was added 1,4-dioxane (9 mL), followed by a solution of K3PO4 (0.54 g, 2.52 mmol, 2.0 eq) in H2O (4.0 mL). The reaction was heated to 150 C for 30 min under microwave irradiation. The reaction was added to EtOAc: H2O (1:1, 100 mL). The organic layer was separated, washed with H2O (25 mL), Brine (25 mL), dried (MgSO4), filtered and concentrated. The material was purified by reverse-phase HPLC (5-35% acetonitrile: H2O w/ 0.1% TFA) to afford 4-(4-(pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)morpholine, 11 (0.25 g, 71% yield).LCMS: RT = 0.560 min, >98% (at) 215 and 254 nM, m/z = 281.1 [M + H]+.

According to the analysis of related databases, 705263-10-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Engers, Darren W.; Frist, Audrey Y.; Lindsley, Craig W.; Hong, Charles C.; Hopkins, Corey R.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 11; (2013); p. 3248 – 3252;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 705263-10-1 ,Some common heterocyclic compound, 705263-10-1, molecular formula is C6H4BrN3, 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.

The mixture of 15a (0.87 g, 4.39 mmol), 4-[4-(tert- butoxycarbonyl)piperazin-l-yl]phenylboronic acid pinacol ester (1.7 g, 4.39 mmol), Pd(Ph3P)4 (0.5 g, 0.439 mmol), K2CO3 (1.82 g, 13.17), 1 ,4-dioxane (15 mL) and H2O (5 mL) was heated at 1 10 C under a nitrogen atmosphere for 5 h in a sealed vial. The reaction mixture was concentrated and the residue was purified by column chromatography using CH2Cl2/EtOAc to give 16 (1.4 g, 86% yield). 1H NMR (CDCl3) delta 8.82 (dd, J = 2.2, 0.7 Hz, IH), 8.77 (d, J = 2.2 Hz, I H), 8.16 (d, J = 2.2 Hz, 1 H), 7.54 (d, J = 8.8 Hz, 2H), 7.08 (d, J = 8.8 Hz, 2H), 6.75 (dd, J = 2.2, 0.7 Hz, 1 H), 3.63 – 3.67 (m, 4H), 3.25 – 3.28 (m, 4H), 1.53 (s, 9H).

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. 705263-10-1, 6-Bromopyrazolo[1,5-a]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; THE BRIGHAM AND WOMEN’S HOSPITAL, INC.; WO2009/114180; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 705263-10-1 , The common heterocyclic compound, 705263-10-1, name is 6-Bromopyrazolo[1,5-a]pyrimidine, molecular formula is C6H4BrN3, 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 1 6-Phenylethynyl-pyrazolo[1,5-a]pyrimidine Bis-(triphenylphosphine)-palladium(II) dichloride (27 mg, 0.04 mmol) was dissolved in 1 ml of THF. 6-Bromo-pyrazolo[1,5-a]pyrimidine (150 mg, 0.76 mmol) and phenylacetylene (130 mul, 1.21 mmol) were added at room temperature. Triethylamine (310 mul, 2.3 mmol), triphenylphosphine (6 mg, 0.023 mmol) and copper(I) iodide (4 mg, 0.023 mmol) were added and the mixture was stirred for 2 hours at 65 C. The reaction mixture was cooled and extracted with saturated NaHCO3 solution and two times with a small volume of dichloromethane. The crude product was purified by flash chromatography by directly loading the dichloromethane layers onto a silica gel column and eluting with heptane:ethyl acetate 100:0->50:50. The desired compound was obtained as a yellow solid (150 mg, 90% yield), MS: m/e=220.3 (M+H+).

The synthetic route of 705263-10-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Green, Luke; Guba, Wolfgang; Jaeschke, Georg; Jolidon, Synese; Lindermann, Lothar; Stadler, Heinz; Vieira, Eric; US2011/152257; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 705263-10-1, 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. 705263-10-1, name is 6-Bromopyrazolo[1,5-a]pyrimidine, molecular formula is C6H4BrN3, 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.

6-Bromo-pyrazolo [1,5-a] pyrimidine (2.0 g, 10.0 mmol) dissolved in 20 mL of toluene, [1,1′-bis (diphenylphosphino) ferrocene Fe] dichloropalladium (0.7 g, 1 mmol), potassium acetate (4.0 g, 40.0 mmol) and the associated acid pinacol ester (5.1 g, 20.0 mmol) were added in the flask. It was heated to reflux under argon for 5 h, and TLC monitoring of the reaction process until the starting material disappeared stop heating. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography (eluent: petroleum ether / ethyl acetate). White solid, yield: 65%. 1H NMR (CDCl3, 400 MHz, delta ppm):8.71 (d, J = 1.6 Hz, 1H), 8.17 (d, J = 2.2 Hz, 1H), 1.38 (s, 12H). ESI-MS(m/z): 246.1 [M+H]+.

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 705263-10-1, 6-Bromopyrazolo[1,5-a]pyrimidine.

Reference:
Article; Hu, Liming; Cao, Tingting; Lv, Yongjuan; Ding, Yiming; Yang, Leifu; Zhang, Qiang; Guo, Mingzhou; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5830 – 5835;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 705263-10-1, 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 705263-10-1 as follows.

Preparative Example 14 Step 1 : 6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrazolo[l,5-a]pyrimidine To a solution of 6-bromopyrazolo[l,5-a]pyrimidine (1.5 g, 7.57 mmol) in 1,4-dioxane (20 mL) were added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (2.12 g, 8.33 mmol), potassium acetate (1.48 g, 15.14 mmol) and l,l’-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (553 mg, 0.76 mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 100 C for 4 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in hexane) affording 6-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrazolo[l ,5-a]pyrimidine (1.0 g, 54%): lU NMR (400 MHz, Chloroform-d) delta 8.99 (s, 1H), 8.69 (s, 1H), 8.15 (d, / = 2.4 Hz, 1H), 6.67 (d, J = 2.4 Hz, 1H), 1.42 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,705263-10-1, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 705263-10-1 ,Some common heterocyclic compound, 705263-10-1, molecular formula is C6H4BrN3, 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 microwave tube, add 6-bromo-pyrazolo [1, 5-a] pyrimidine (0.175 g, 0.884 MMOL), 2-(PYRIDIN-2-YL)-5, 6-DIHYDRO-4H-PYRROLO [1, 2-b] pyrazole-3-boronic acid (0.25 g, 1.09 mmol), tetrakis (triphenylphosphine) palladium (0) (31 mg, 0.027 mmol), 2M aqueous potassium carbonate (0.5 mL, 1.0 mmol) and dimethylsulfoxide (1.5 mL). Irradiate the reaction in a microwave reactor set at 110 C, 50 Watts, 10 min with external cooling. Dilute the reaction mixture with diethyl ether (250 mL) and extract the product into 0. 1M aqueous hydrochloric acid (450 mL). Make the aqueous solution basic by adding 5M aqueous sodium hydroxide (25 mL) and extract with dichloromethane (300 mL). Filter the organic layer and concentrate under reduced pressure. Recrystallize the resulting solid from ethyl acetate, filter, rinse with ethyl acetate, and dry at 100 C under vacuum to obtain 70 mg (26%) of the title compound as a tan solid. MS (electrospray, m/z) 302.9 (M+1).

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. 705263-10-1, 6-Bromopyrazolo[1,5-a]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/50659; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia