Category: 55405-67-9

Related Products of 55405-67-9 ,Some common heterocyclic compound, 55405-67-9, 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.

Water (160 mL) was added dropwise at room temperature to a mixture of 4-ethoxycarbonylphenylboronic acid (50 g, 0.26 mol), 3-bromopyrazolo[1,5-a]pyrimidine (56.25 g, 0.28 mol), Pd(ddpf)Cl2.CH2Cl2 (4.25 g, 5.21 mmol), and Cs2CO3 (169.42 g, 0.52 mol) in 1,4-dioxane (1 L). The reaction mixture was then heated 85 C. for 4 h. The reaction mixture was cooled, poured into water and extracted with EtOAc (2×300 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with a gradient of petroleum ether: EtOAc (100:10 to 3:1) to deliver the title compound (64 g, 93%) as a yellow solid. [0400] 1H NMR (400 MHz, CDCl3) delta 8.73 (d, 1H), 8.63 (d, 1H), 8.52 (s, 1H), 8.20-8.09 (m, 4H), 6.92 (dd, 1H), 4.41 (q, 2H), 1.43 (t, 3H).

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. 55405-67-9, 3-Bromopyrazolo[1,5-a]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; Darout, Etzer; Dullea, Robert; Hawkins, Julie Jia Li; Londregan, Allyn T.; Loria, Paula M.; Maguire, Bruce; McClure, Kim F.; Petersen, Donna N.; Piotrowski, David W.; US2014/315928; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 55405-67-9, 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 55405-67-9, name is 3-Bromopyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

PREPARATION 107 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine A mixture of 3-bromopyrazolo[1,5-a]pyrimidine (1.00 g, 5.1 mmol), potassium acetate (1.78 g, 18.1 mmol) and bis(pinacolato)diboron (5.77 g, 22.7 mmol) in 1,4-dioxane (20 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and bis(triphenylphosphine)palladium(II) dichloride (0.180 g, 0.26 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated to 100 C. After 20 hours, the reaction mixture was cooled, evaporated and then taken up in pentane and filtered through diatomaceous earth (Celite) and the filter cake was washed with a mixture of ethyl acetate/ether (3:2). The combined filtrate and washings were evaporated and the residue was stirred with n-pentane (15 mL) at -40 C for 30 minutes. The solid was filtered, washed with cold pentane and dried in vacuo to give the title compound (1.66 g, >100%) as a solid which was used without further purification. LRMS (m/z): 246 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm 1.26 (s, 12H), 6.89 (dd, 1H), 8.44 (s, 1H), 8.63 – 8.83 (m, 2H).

According to the analysis of related databases, 55405-67-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; GOMEZ CASTILLO, Elena; BACH TANA, Jordi; WO2011/157397; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 55405-67-9, 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. 55405-67-9, name is 3-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.

General procedure: To a solution of 6-bromopyridine-2-carbonitrile (80 mg, 0.44 mmol) and 4-(morpholin-4-yl)-5-(4,4, 5, 5-tetramethyl- 1, 3,2-d ioxaborolan-2-yl )-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (P2) (241 mg, 0.523 mmol) in1,4-dioxane (2.5 mL) and water (0.5 mL) was addedtetrakis(triphenylphosphine)palladium(0) (51 mg, 44 pmol) and sodium carbonate (140 mg, 1.32 mmol). The reaction mixture was heated at 120 C under microwave irradiation for 15 minutes, then diluted with water (30 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (100 mL), dried over sodium sulfate, filtered, and concentratedin vacuo; purification via preparative thin layer chromatography (Eluent: 1:1 petroleum ether ethyl acetate) afforded the product as a brown oil. Yield: 110 mg, 0.252 mmol, 57%. 1H NMR (400 MHz, CDCl3) 8.52 (s, 1H), 7.84-7.93 (m, 2H), 7.74 (s, 1H), 7.59 (dd, J=7.0, 1.2 Hz, 1H), 5.66 (s, 2H), 3.56-3.65 (m, 6H), 3.34-3.40 (m, 4H), 0.93 (dd, J8.3, 8.0 Hz, 2H), -0.05 (s, 9H).

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 55405-67-9, 3-Bromopyrazolo[1,5-a]pyrimidine.

Reference:
Patent; PFIZER INC.; GALATSIS, Paul; HAYWARD, Matthew Merrill; HENDERSON, Jaclyn; KORMOS, Bethany Lyn; KURUMBAIL, Ravi G; STEPAN, Antonia Friederike; VERHOEST, Patrick Robert; WAGER, Travis T.; ZHANG, Lei; WO2014/1973; (2014); 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.55405-67-9, name is 3-Bromopyrazolo[1,5-a]pyrimidine, molecular formula is C6H4BrN3, molecular weight is 198.0201, as common compound, the synthetic route is as follows.COA of Formula: C6H4BrN3

A solution of 3-bromopyrazolo[1,5-ajpyrimidine (0.04 g, 0.202 mmol), (8)- tert-butyl (2,4-dimethyl- 1 -(4-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)-2- (trifluoromethyl)phenoxy)pentan-2-yl)carbamate (prepared as described in Example 255, Parts A and B) (0.122 g, 0.242 mmol), and potassium phosphate tribasic (0.106 g, 0.606 mmol) in THF (5 mL) and water (0.5 mL) was purged with nitrogen gas for30 mi XPhos generation precatalyst (9.37 mg, 0.030 mmol) was added to the reaction mixture and the solution was purged with nitrogen gas again for 10 mm. The reaction mixture was heated at 80C 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 andthe diatomaceous earth was washed with ethyl acetate (50 mL). The ethyl acetate layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford (S)-tert-butyl (2,4-dimethyl-1-(4-(pyrazolo[1,5-ajpyrimidin-3-yl)- 2-(trifluoromethyl)phenoxy)pentan-2-yl)carbamate (50 mg, 0.102 mmol, 50% yield) as a brown solid which was carried forward without further purification. LCMS(ESI) m/e 493.3 [(M+H), calcd for C25H32F3N403 493.21; LC/MS retention time (Method Al): tR = 1.83 mm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55405-67-9, 3-Bromopyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

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

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 55405-67-9, name is 3-Bromopyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 55405-67-9

Weigh into a round bottom flask 3-bromopyrazolo [1, 5-a] pyrimidine (Lynch et al. Can. J. Chem. 1975, 53, 119-122; 0.095 g, 0.48 mmol), 2- (pyridin-2-yl)-5, 6-dihydro- 4H-pyrrolo [1, 2-b] pyrazole-3-boronic acid (Preparation 5; 0.10 g, 0.44 MMOL), triphenylphosphine (Aldrich; 0.007 g, 0.027 mmol) and tris (dibenzylideneacetone) dipalladium (0) (Aldrich; 0.015 g, 0.016 mmol). Add p-dioxane (6 ml) and 2. 0M aqueous potassium carbonate (2 mL). Stir and reflux under nitrogen for 6 h. Dilute with ethyl acetate, separate the organic layer, concentrate under reduced pressure, and chromatograph on flash silica using neat acetonitrile. Purify on a preparative reverse phase C-18 high-performance chromatography column using a gradient from 5% to 100% acetonitrile in 0.03% aqueous hydrochloric acid. Concentrate the pure fractions under reduced pressure, dissolve the residue in distilled water, and make basic by adding 1. OM aqueous sodium hydroxide. Extract with dichloromethane, dry the organic layer over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain 6 mg (4.5%) of the title compound as a yellow solid. TOF MS ES+ exact mass calculated for C17HL5N6 (MA : m/z = 303.1358 ; Found: 303. 1371.’H NMR (400 MHz, CDCL3) 8 8.66 (d, J = 2 Hz, 1H), 8. 64 (d, J = 2 Hz, 1H), 8.41 (dd, J = 4,2 Hz, 1H), 8.31 (s, 1H), 7.70 (M, 2H), 7.21 (M, 1H), 6.79 (dd, J = 7,4 Hz, 1H), 4.30 (t, J = 7 Hz, 2H), 3.10 (t, J = 8 Hz, 2H), 2.68 (M, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 55405-67-9.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/50659; (2004); 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. 55405-67-9, name is 3-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. Product Details of 55405-67-9

PREPARATION 107 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine [Show Image] A mixture of 3-bromopyrazolo[1,5-a]pyrimidine (1.00 g, 5.1 mmol), potassium acetate (1.78 g, 18.1 mmol) and bis(pinacolato)diboron (5.77 g, 22.7 mmol) in 1,4-dioxane (20 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and bis(triphenylphosphine)palladium(II) dichloride (0.180 g, 0.26 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated to 100 C. After 20 hours, the reaction mixture was cooled, evaporated and then taken up in pentane and filtered through diatomaceous earth (Celite) and the filter cake was washed with a mixture of ethyl acetate/ether (3:2). The combined filtrate and washings were evaporated and the residue was stirred with n-pentane (15 mL) at -40 C for 30 minutes. The solid was filtered, washed with cold pentane and dried in vacuo to give the title compound (1.66 g, >100%) as a solid which was used without further purification. LRMS (m/z): 246 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm 1.26 (s, 12H), 6.89 (dd, 1H), 8.44 (s, 1H), 8.63 – 8.83 (m, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 55405-67-9.

Reference:
Patent; Almirall, S.A.; EP2397482; (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.55405-67-9, name is 3-Bromopyrazolo[1,5-a]pyrimidine, molecular formula is C6H4BrN3, molecular weight is 198.0201, as common compound, the synthetic route is as follows.COA of Formula: C6H4BrN3

To a stirred solution of compound 13f (27.8 mmol) in 1,4-dioxane (120 mL) was added B2Pm2 (126 mmol) and KOAc (101 mmol) at rt. The resulting mixture was purged with Ar for 45min, PdCl2(PPli3)2 (1.5 mmol) was added and the mixture again purged with Ar for 30min. The resulting mixture was heated to 1000C for 15h. The reaction mixture was concentrated to obtain a viscous mass, which was charged over afluorosil plug, washed with pentane, followed by 60% EtOAc/Pet ether. The relevant fractions were concentrated to obtain a crude compound 13g as a pale yellow solid. The crude compound 13g was stirred with pentane (25mL) at -400C for 30min, filtered, washed with cold pentane (5mL) and dried under vacuum to obtain sufficiently pure compound (3.5g, 51.4%). TLC system: Ethyl acetate: Petroleum ether (2:3) Rf value: 0.4. (M + H): 246.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55405-67-9, 3-Bromopyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/85913; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia