Category: 374930-88-8

Application of 374930-88-8, Adding some certain compound to certain chemical reactions, such as: 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate,molecular formula is C13H19BrN4O2, 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 374930-88-8.

Synthesis of tert-butyl 4-(5-acetylpyrimidin-2-yl)piperazine-1-carboxylate To a mixture of tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (5.0 g, 14.6 mmol), palladium diacetate (240 mg, 1.46 mmol) and triphenylphosphine (376 mg, 2.92 mmol) in dioxane (100 mL) was added tributyl(1-ethoxyvinyl)stannane (5.3 mL, 16.1 mL) under N2, and the reaction mixture was stirred at 80 C. overnight. The reaction was cooled to RT and diluted with THF (100 mL), followed by the addition of 2 N HCl (100 mL). The mixture was stirred at RT for 30 mins, and LCMS showed the reaction was completed. The reaction mixture was diluted with ethyl acetate (200 mL). The organic phase was separated, washed with water (3*100 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography to afford the title compound (3.0 g, 67%). MS (ES+) C15H22N4O3 requires: 306, found: 251 [M-56+H]+.

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. 374930-88-8, tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Hodous, Brian L.; Kim, Joseph L.; Miduturu, Chandrasekhar V.; Wilson, Douglas; Zhang, Yulian; US2015/111857; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 374930-88-8, 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 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Synthesis of tert-butyl 4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazine-1-carboxylate In a sealed tube, the mixture of tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (1.0 g, 2.9 mmol), ethynylcyclopropane (482 mg, 7.3 mmol), tetrakis(triphenyl-phosphine)palladium (335 mg, 0.29 mmol) and copper(I) iodide (28 mg, 0.15 mmol) in diethylamine (10 mL) and dimethyl sulfoxide (10 mL) was stirred at 100 C. for 3 hours under nitrogen atmosphere. The mixture was then diluted with ethyl acetate (100 mL) and washed with water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography eluting with petroleum ether:ethyl acetate=15:1 to afford tert-butyl 4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazine-1-carboxylate (930 mg, 98%) as a yellow solid. MS (ES+) C18H24N4O2 requires: 328, found: 329 [M+H]+.

According to the analysis of related databases, 374930-88-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Hodous, Brian L.; Kim, Joseph L.; Miduturu, Chandrasekhar V.; Wilson, Douglas; Zhang, Yulian; US2015/111857; (2015); 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 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C13H19BrN4O2

To a stirred solution of tert-butyl-4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (15.0 g, 43.7 mmol) in 1,4-dioxane (50 mL), HCI in dioxane (150 mL, 10V, 4N) was added at 0 C and stirred at rt for 4 h. The resulting white precipitate was filtered and was washed with Et2O (25 mL), EtOAc (2 x 20 mL) to afford the title product. Yield: 98.2% (12.0 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 9.40 (br s, 2H), 8.54 (s, 2H), 3.93 (t, J = 4.8 Hz, 4H), 3.13 (br s, 4H). LCMS: (Method A) 244.9 (M -35), Rt. 1.71 min, 99.8 % (Max).

With the rapid development of chemical substances, we look forward to future research findings about 374930-88-8.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 374930-88-8 ,Some common heterocyclic compound, 374930-88-8, molecular formula is C13H19BrN4O2, 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.

tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (0.242 g, 0.705 mmol) was taken up in THF (3.5 mL) and cooled to -78 C. A solution of nBuLi, 2.5 M in hexanes (0.31 mL, 0.775 mmol) was added at a fast dropwise rate from a syringe. The resulting mixture was stirred at -78 C. for 15 minutes. A solution of (R,Z)-2-methyl-N-(2,2,2-trifluoro-1-(4-fluorophenyl)ethylidene)propane-2-sulfinamide (0.225 g, 0.762 mmol) in THF (0.5 mL) was added at a fast dropwise rate from a syringe. The reaction mixture was stirred at -78 C. for 5 minutes before warming to room temperature. After 45 minutes, saturated NH4Cl was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by MPLC (0-80% EtOAc-hexanes) gave tert-butyl 4-(5-((S)-1-(((R)-tert-butylsulfinyl)amino)-2,2,2-trifluoro-1-(4-fluorophenyl)ethyl)pyrimidin-2-yl)piperazine-1-carboxylate (304 mg, 0.543 mmol, 77% yield) as a pale yellow gum. The absolute stereochemistry was assigned randomly. MS (ES+) C25H33F4N5O3S requires: 559. found: 560 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,374930-88-8, its application will become more common.

Reference:
Patent; Hodous, Brian L.; Kim, Joseph L.; Wilson, Kevin J.; Wilson, Douglas; Zhang, Yulian; US2015/111887; (2015); 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. 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, molecular formula is C13H19BrN4O2, 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. SDS of cas: 374930-88-8

To a solution of dicyclohexylamine (3.43 g, 18.94 mmol) in THF (60 mL) at -78 C. was added n-BuLi (2.5 M, 7.9 mL, 18.94 mmol) dropwise. The mixture was stirred at RT for 10 min, followed by the addition of methyl 2-(4-fluorophenyl)acetate (2.69 g, 16.02 mmol) in toluene (60 mL). After stirred at RT for another 10 min, tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (5.0 g, 14.57 mmol), Pd2(dba)3 (667 mg, 0.728 mmol) and P(t-Bu)3 (10%, 1.47 g, 0.728 mmol) were added sequentially. The reaction mixture was stirred at RT for 15 h, quenched by water (150 mL) and extracted with EA. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was passed a column (silica gel, PE_EA=6:1) to afford the title compound (0.5 g, 8%) as an orange solid. MS (ES+) C22H27FN4O4 requires: 430. found: 431 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 374930-88-8.

Reference:
Patent; Hodous, Brian L.; Kim, Joseph L.; Wilson, Kevin J.; Wilson, Douglas; Zhang, Yulian; US2015/111887; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 374930-88-8, 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.374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, molecular formula is C13H19BrN4O2, molecular weight is 343.2196, as common compound, the synthetic route is as follows.

General procedure: In a dried microwave reactor vessel were added 3-bromoquinoline(0.204 mL, 1.5 mmol), Pd(dba)2 (86 mg, 0.15 mmol), K2CO3carbonate (415 mg, 3.00 mmol), S-Phos (185 mg, 0.45 mmol), dryD8-IPA (0.500 mL) and MeCN (1 mL). The mixture was degassedand placed under a nitrogen atmosphere. The sealed reaction tubewas heated to 100 C in a microwave (Biotage Initiator) for 2.5 h.The solvents were removed under reduced pressure, the crudematerial pre-loaded on to silica and purified using flash silica chromatography(15% EtOAc/heptane). The fractions containing thedesired compound were combined and evaporated to dryness toafford 3-deuterioquinoline (140 mg, 72%); 1H NMR (400 MHz,DMSO, 27 C): d (ppm) 7.62 (ddd, J = 1.20, 6.89, 8.11 Hz, 1H), 7.77(ddd, J = 1.50, 6.87, 8.43 Hz, 1H), 7.99 (dd, J = 1.33, 8.18 Hz, 1H),8.03 (d, J = 8.41 Hz, 1H), 8.37 (s, 1H), 8.91 (d, J = 1.70 Hz, 1H); 13CNMR (176 MHz, DMSO, 30 C) 121.0, 126.4, 127.8, 128.0, 128.8,129.3, 135.8, 147.7, 150.3; HRMS (EI): M+, found 130.0643,C9H6DN requires 130.0641.

The chemical industry reduces the impact on the environment during synthesis 374930-88-8, I believe this compound will play a more active role in future production and life.

Reference:
Article; Donald, Craig S.; Moss, Thomas A.; Noonan, Gary M.; Roberts, Bryan; Durham, Emma C.; Tetrahedron Letters; vol. 55; 22; (2014); p. 3305 – 3307;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 374930-88-8 , The common heterocyclic compound, 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, molecular formula is C13H19BrN4O2, 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.

Tri-isopropyl borate (1.18 g, 6.25 mmol) was added, dropwise to a magnetically stirred solution of 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (1.72 g, 5.00 mmol) in THF (15 mL). The mixture was cooled to -70 oC and butyl lithium (3.91 mL, 6.25 mmol) was added, dropwise maintaining the temperature at -60 oC over 15 minutes. The mixture was then warmed to -20 oC over 20 minutes followed by the addition of acetic acid (0.501 mL, 8.75 mmol). The reaction mixture was then evaporated and the resultant residue suspended in methanol (2 mL) and water (15 mL) to which hydrogen peroxide (0.870 mL of a 35% w/v solution in water, 49.4 mmol) was introduced, dropwise with vigorous stirring. The reaction was stirred for 18 hours and the resultant precipitate was filtered and washed with water. The solid was partitioned between dichloromethane and water and the separated organic phase was dried (MgSO4), filtered and concentrated to yield tert-butyl 4-(5-hydroxypyrimidin-2-yl)piperazine-1-carboxylate (1.32 g, 92%) as a white solid, NMR Spectrum: (DMSOd6) 1.46 (s, 9H), 3.43 (m, 4H), 3.61 (m, 4H), 8.09 (S, 2H), 9.30 (s, 1H); Mass Spectrum: M+H+ 281.

The synthetic route of 374930-88-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; De Savi, Chris; Waterson, David; Pape, Andrew; Lamont, Scott; Hadley, Elma; Mills, Mark; Page, Ken M.; Bowyer, Jonathan; Maciewicz, Rose A.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 16; (2013); p. 4705 – 4712;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 374930-88-8, 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 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: ferf-Butyl 4-(5-cyanopyrimidin-2-yl)piperazine-l -carboxylate; Into a 200 mL pressure flask equipped with a magnetic stir bar was added tert- butyl 4-(5-bromopyrimidin-2-yl)piperazine-l-carboxylate (5.0 g, 14.6 mmol) and DMF (73 mL). Copper(I) cyanide (2.6 g, 29.0 mmol) was added and the flask was sealed and heated to 140 0C for 19 h. The reaction mixture was diluted with water (100 mL) and EtOAc (75 mL) and filtered through a short plug of celite on a sintered glass funnel under vacuum. The filtrate was poured into a 250 mL separatory funnel containing water (50 mL) and the aqueous layer was extracted with EtOAc (3 x 75 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by column chromatography through silica gel, eluting with 0% EtOAc in hexanes to 40% EtOAc in hexanes as a gradient provided the desired compound. MS (ESI, Q+) m/z 312 (M + Na).

According to the analysis of related databases, 374930-88-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK FROSST CANADA LTD.; ISABEL, Elise; LACHANCE, Nicolas; LECLERC, Jean-Philippe; LEGER, Serge; OBALLA, Renata, M.; POWELL, David; RAMTOHUL, Yeeman, K.; ROY, Patrick; TRANMER, Geoffrey, K.; ASPIOTIS, Renee; LI, Lianhai; MARTINS, Evelyn; WO2010/94126; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 374930-88-8, 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. 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, molecular formula is C13H19BrN4O2, 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.

A mixture of tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (684 mg, 2.0 mmol), 4-fluorophenol (1.1 g, 5.0 mmol), copper (650 mg, 10.0 mmol) and Cs2CO3 (6.5 g, 20.0 mmol) in pyridine (15 mL) was heated at 120 C. for 12 h. The mixture was cooled to RT, diluted with ethyl acetate (200 mL) and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=20/1) to afford the title compound (200 mg, 27%) as a brown solid. MS (ES+) C19H23FN4O3 requires: 374. found: 319 [M-56+1]+.

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 374930-88-8, tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate.

Reference:
Patent; Hodous, Brian L.; Kim, Joseph L.; Wilson, Kevin J.; Wilson, Douglas; Zhang, Yulian; US2015/111887; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia