Category: 90914-41-3

Adding a certain compound to certain chemical reactions, such as: 90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]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, Quality Control of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, blongs to pyrimidines compound. Quality Control of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

a) 3-bromo-4-chloro-1-(phenylsulfon -1 H-pyrazolo[3,4-c ]pyrimidineTo a dry 500 mL flask was added 3-bromo-4-chloro-1 H-pyrazolo[3,4-d]pyrimidine (4 g, 17.13 mmol) in THF (160 mL). DMF (10 mL) was added and the stirred contents were cooled to 0 C. NaH (60% dispersion in oil, 0.82 g, 20 mmol) was added portionwise and the mixture was stirred for 15 min. Benzene sulfonyl chloride (2.4 mL, 18.8 mmol) was added dropwise via syringe. After stirring for 15 min, the reaction vessel was removed from an ice bath. After 2 h, the contents were poured onto ice-water (50 mL), and stirred for 30 min. The white precipitate was filtered and washed with water to afford 4.38 g of a white solid. The mother liquor was concentrated down, extracted thrice with EtOAc and evaporated to dryness. The residue was triturated with EtOAc to afford an additional 1.3 g of the title compound. A total weight of 5.68 g of title compound was obtained (89%). LCMS(ES) m/e 373, 375 (M, M+2); 1H NMR (400 MHz, DMSO-d6) delta ppm 9.1 1 (s, 1 H), 8.1 1 (dd, J = 1.14, 8.46 Hz, 2H), 7.84 (s, 1 H), 7.71 (d, J = 8.34 Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; HAMMOND, Marlys; KALLANDER, Lara, S.; LAWHORN, Brian, Griffin; PHILP, Joanne; SARPONG, Martha, A.; SEEFELD, Mark, Andrew; WO2011/149827; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]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, 90914-41-3, blongs to pyrimidines compound. Computed Properties of C5H2BrClN4

The resulting de- boc’ed residue was dissolved in TEtaF (5mL), and Et3N (0.1 mL) before adding 3-Bromo-4- Chloro-lH-pyrazolo[3,4-Patent; EXELIXIS, INC.; WO2006/71819; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 90914-41-3, 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. 90914-41-3, name is 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H2BrClN4, 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.

To a solution of N-Boc-4-(p-chlorophenyl)-piperidine-4-carbamide (135 mg, 0.40 mmol) in DMF (4 mL) was added NaH (60% in mineral oil, 20 mg, 0.5 mmol). The stirring was continued for 30 min. Then 3-(diethylamino)propyl chloride (90 mg, 0.60) was added. The mixture was then warmed to 90 0C. The stirring was continued for another 3 h. To the cooled mixture was added H2O. It was then extracted with EtOAc. The organic phase was washed with brine, and dried over Na2SO4. Removal of EtOAc gave the crude product. The crude product (about 0.4 mmol) obtained above was treated with excess TFA in DCM for 30 min. Upon removal of excess TFA and DCM, the residue was free-based and then reacted with 3-Bromo-4-chloro-lH-pyrazolo[3,4-d]pyrimidine (40 mg, 0.17 mmol) in the presence of Et3N (152 mg, 1.5 mmol) in 1,4-dioxane (2 mL) at 70 0C for 1 h. The mixture was concentrated. The crude product was purified by preparation EtaPLC. LC-MS (M+l): 550.4 (100%), 548.4 (80%).1H NMR (400 MHz, DMSO-d6) delta 8.31 (s, 1 H), 7.83 (t, J = 5.5 Hz, 1 H), 7.41 (s, 4 H), 4.25 (br d, J = 13.4 Hz, 2 H), 3.37 (br t, J = 11.9 Hz, 2 H), 3.08 (q, J = 6.4 Hz, 2 H), 2.63 (br d, J = 13.7 Hz, 2 H), 2.34 (q, J = 7.2 Hz, 4 H), 2.23-2.19 (m, 2 H), 1.99-1.92 (m, 2 H), 1.49-1.41 (m, 2 H), 0.85 (t, J = 7.2 Hz, 6 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 90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Patent; EXELIXIS, INC.; WO2006/71819; (2006); 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 90914-41-3, name is 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H2BrClN4

Bromopyrazolopyrimidine (8) To a 25 mL recovery flask were added 6 (230 mg, 0.708 mmol, 1.05 eq.), THF (10 mL), Et3N (470 muL, 3.37 mmol, 5.0 eq.), and chloropyrazolopyrimidine 7 EPO (157 mg, 0.674 mmol, 1.0 eq.). The reaction mixture was stirred at reflux for 1.5h. The reaction was concentrated and diluted with EtOAc (50 mL) and NaHCO3 (sat’d aq., 50 niL). The organic layer was washed with H2O (50 mL) and brine (50 mL). The combined aqueous layers were extracted with EtOAc (2 x 50 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated to give a light-brown oil that slowly solidified to a white solid (308 mg crude). The crude material was purified via flash chromatography (10% to 20% CH3OH/CH2C12) to give a colorless oil (205 mg, 58%).Observed M+H: 523.1 (Br isotope)NMR, DMSO-d6, HCl salt : deltaltheta.40 (s, IH), 8.30 (s, IH), 7.49 (d, 2H), 7.26 (d, 2H), 4.88 (s, IH), 4.59 (m, 2H), 4.50 (obs m, 2H), 3.34-3.23 (m, 4H), 3.07-3.03 (m, 2H), 2.73 (s, 6H), 1.94 (d, 2H), 1.38-1.34 (m, 2H) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 90914-41-3.

Reference:
Patent; EXELIXIS, INC.; WO2006/71819; (2006); 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. 90914-41-3, name is 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

To a stirred solution of 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (3.5 g, 15.02 mmol, 1 equiv) in DMF (60 mL) was added sodium hydride (0.72 g, 18.02 mmol, 1.2 equiv) at 0C. The reaction mixture was stirred for 15 mm at 0C. Methyl iodide (1.12 mL, 18.02 mmol, 1.2 equiv) was added to the reaction mixture at 0C. The reaction mixture was warmed to room temperature and stirred for 3h. The reaction mixture was quenched with ice water and extracted in ethyl acetate. The organic layer was dried over sodium sulphate and evaporated to obtain crude product, which was purified over silica gel flash column chromatography. The compound eluted out in 30% EtOAc in n-Hexane. Fractions obtained were concentrated to give 3-bromo-4-chloro- 1-methyl-i H-pyrazolo[3,4- d]pyrimidine (2.0 g, 57%) as pale yellow solid. LCMS (ES) m/z = 247.4, 249.4 [M+H. ]. 1H NMR (400 MHz, DMSO-d6) O ppm -4.03 (5, 3H), 8.88 (5, 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, 90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey Michael; FAUCHER, Nicolas Eric; DAUGAN, Alain Claude-Marie; (110 pag.)WO2017/46738; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 90914-41-3, 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. 90914-41-3, name is 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below.

A microwave tube containing 19.3 mg of 5-phenyl-o-anisidine (0.097 mmol), 25.1 mg of 3-bromo-4-chloro-lH-pyrazolo[3,4-d]pyrimidine (0.11 mmol), 9.2 mu^ of glacial acetic acid (0.16 mmol) and 1 mL of n-butanol with a stir bar was capped and heated to 130C for 15 min in a microwave reactor. The reaction was cooled and concentrated by rotary evaporation. The residue was recrystallized in ethanol to give 30.7 mg of crude 4 as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SHEN, Weijun; NOVOTNY, Christopher; SHOKAT, Kevan, M.; (490 pag.)WO2017/184775; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]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, Recommanded Product: 90914-41-3, blongs to pyrimidines compound. Recommanded Product: 90914-41-3

Step 5: Synthesis of 4-(4-((1-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperidin-4-yl)amino)-6-methoxynaphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (144): To a solution of 4-(6-methoxy-4-(piperidin-4-ylamino)naphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (143) (196 mg, 0.43 mmol) and triethylamine (0.5 ml) in anhydrous tetrahydrofuran (8 ml) was added 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (122 mg, 0.52 mmol). The mixture was stirred at 50 C. for 24 hours before being poured into ethyl acetate (150 ml) washed with water (300 ml) and the organic layer dried over anhydrous magnesium sulfate. Evaporation to dryness gave a yellow foam that was crystallized from dichloromethane and ethyl acetate to give 4-(4-((1-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperidin-4-yl)amino)-6-methoxynaphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (144) as a yellow solid (145 mg) M.p.=167-172 C. 1H NMR (DMSO-d6) 400 MHz delta 8.4-8.33 (m, 2H), 7.9-7.8 (m, 2H), 7.52 (m, 2H), 7.24-7.2 (m, 1H), 7.15-7.12 (m, 1H), 5.9-5.74 (m, 1H), 4.56-4.53 (m, 2H), 3.95 (s, 1H), 3.9 (s, 3H), 3.41-3.26 (m, 2H), 3.22 (s, 6H), 2.28-2.25 (m, 2H), 1.97-1.75 (m, 2H), LCMS m/e 574 and 576 (M+) Calculated for C27H28BrN9O.CH2Cl2: C, 51.00; H, 4.59; N, 19.12; found C 51.00, H 4.39, N 18.85.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ArQule, Inc.; US2011/166137; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]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, Quality Control of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, blongs to pyrimidines compound. Quality Control of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

1-(1-benzyl-4-piperidinyl)-3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (Intermediate C) 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (Intermediate B) (5.0 g, 21.42 mmol), 1-benzyl-4-piperidinol (8.2 g, 42.83 mmol) and triphenylphosphine (11.23 g, 42.83 mmol)were suspended in 250 ml of tetrahydrofuran. The reaction mixture was cooled in an ice-water bath and diethyl azodicarboxylate (6.8 ml, 42.83 mmol) was added dropwise. 10 minutes later, the reaction mixture was allowed to warm up to room temperature. After stirring for 2 hours, solvent was removed and the residue was taking into ethyl acetate. The organic layer was washed, dried and evaporated. The crude product was passed through Biotage flash column using dichloromethane/ethyl acetate (90:10) as the mobile phase to yield 10.56 g of 1-(1-benzyl-4-piperidinyl)-3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. The product was 61% pure with a HPLC retention time of 12.46 min. (HPLC condition: 5 to 95% CH3CN in 0.1 N aqueous ammonium acetate over 20 min., the column size is 3.9*150 mm, 300 A).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Abbott Laboratories; US2002/156081; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia