Category: 3177-24-0

Related Products of 3177-24-0 , The common heterocyclic compound, 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile, molecular formula is C5HCl2N3, 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.

2,4-Dichloropyrimidin-5-carbonitrile (1.00 g, 5.75 mmol) was dissolved in 30 mL DMF. To it were added (R)-2-aminobutanamide hydrochloride (1.20 g, 8.62 mmol) and DIEA (3.0 mL, 17.24 mmol). The mixture was stirred at 50°C for 10 m to afford two coupling product in about equal amount in quantitative yield. The mixture was concentrated in vacuo, diluted with EtOAc, washed with brine twice, dried, concentrated and subjected to flash column to separate (R)-2-((4-chloro-5-cyanopyrimidin-2-yl)amino)butanamide.The mixture of (R)-2-((4-chloro-5-cyanopyrimidin-2-yl)amino)butanamide (400 mg, 1.7 mmol), 3-methylisothiazol-5-amine hydrochloride (770 mg, 5.1 mmol), fine powder Cs2C03 (3.88 g, 11.9 mmol), BINAP (212 mg, 0.34 mmol) and Pd(OAc)2 (77 mg, 0.34 mmol) in 50 mL dioxane was degassed using argon stream and stirred at 105°C under argon atmosphere for 6 h. It was diluted with 400 mL EtOAc, vigorously stirred, filtered through celite, concentrated in vacuo and subjected to flash column to isolate (R)-2-((4-chloro-5-cyanopyrimidin-2- yl)amino)butanamide (210 mg).

The synthetic route of 3177-24-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong J.; KANE, Brian; XU, Qing; BAUER, Shawn M.; SONG, Yonghong; PANDEY, Anjali; DICK, Ryan; WO2013/78468; (2013); A1;,
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Synthetic Route of 3177-24-0, 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. 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below.

Example 287: Preparation of 4-(cyclopropylamino)-2-((2-oxo-l,2,3,4-tetrahydroquinolin-6- yl)amino)pyrimidine-5-carbonitrile and 2-(cyclopropylamino)-4-((2-oxo-l,2,3>4- tetrahydroquinolin-6-yl)amino)pyrimidine-5-carbonitrile.2,4-Dichloropyrimidine-5-carbonitrile (0.100 g, 0.575 mmol), cyclopropanamine (0.040 ml, 0.575 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.1 10 ml, 0.632 mmol) were mixed in acetonitrile (2 ml). The mixture was microwaved at 70 °C for 10 min and then concentrated. 6- amino-3,4-dihydroquinolin-2(l H)-one (0.093 g, 0.575 mmol) and acetic acid (0.035 g, 0.575 mmol) were added. The mixture was microwaved at 1 10 °C for 20 min and then concentrated. 14 mg of 4-(cyclopropylamino)-2-((2-oxo- l ,2,3,4-tetrahydroquinolin-6-yl)amino)pyrimidine-5- carbonitrile and 14 mg of 2-(cyclopropylamino)-4-((2-oxo-l ,2,3,4-tetrahydroquinolin-6- yl)amino)pyrimidine-5-carbonitrile were recovered after automated reverse phasechromatography (water-MeCN). MS calcd for [Ci7Hi6N60+H]+: 321.15 found 321.00.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3177-24-0, its application will become more common.

Reference:
Patent; SALK INSTITUTE FOR BIOLOGICAL STUDIES; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; YALE UNIVERSITY; SHAW, Reuben J.; EGAN, Daniel F.; COSFORD, Nicholas; TURK, Benjamin; VAMOS, Mitchell; PANICKAR, Dhanya Raveendra; CHUN, Matthew; SHEFFLER, Doug; (315 pag.)WO2016/33100; (2016); A1;,
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Related Products of 3177-24-0, 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 3177-24-0 as follows.

2-Chloro-4-methoxy-pyrimidine-5-carbonitrile (2) (1160) To a solution of 2,4-dichloro-pyrimidine-5-carbonitrile (1) (300 mg, 1.72 mmol) in THF (anhydrous, 20 mL) was added sodium methoxide solution (0.5 M/MeOH, 3.45 mL, 1.72 mmol). The reaction was stirred at r.t. for 30 minutes. The volatile components were removed in vacuo. Purification was accomplished by Biotage silica gel chromatography (2percent-30percent EtOAc/hexanes gradient) to give 130 mg (45percent yield) of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.62 (s, 1H), 4.18 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3177-24-0, its application will become more common.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; US2015/291629; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3177-24-0, 2,4-Dichloropyrimidine-5-carbonitrile, 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, name: 2,4-Dichloropyrimidine-5-carbonitrile, blongs to pyrimidines compound. name: 2,4-Dichloropyrimidine-5-carbonitrile

Followingthe preparation protocol of Section 5.1.2.1, the reaction mixtureof 2,4-dichloropyrimidine-5-carbonitrile (8d) (367 mg, 2.0mmol), K2CO3 (552 mg, 4.0 mmol) and phenol (188 mg, 2.0 mmol)in acetone (10 mL) was stirred at room temperature for 7 h to givecompound 9f as a white solid (408 mg, 88.0percent); mp 94?96 C; 1HNMR (400 MHz, Acetone d6) d (ppm) 9.08 (s, 1H), 7.54 (t, J = 7.2Hz, 2H), 7.41?7.35 (m, 3H); HRMS (ESI): m/z, Calcd. for C11H7ON3-Cl [M+H]+: 232.0272, Found 232.0270

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3177-24-0, 2,4-Dichloropyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Cui, Guonan; Jin, Jing; Chen, Hualong; Cao, Ran; Chen, Xiaoguang; Xu, Bailing; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 2186 – 2197;,
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Reference of 3177-24-0, 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 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

A solution of Intermediate 43 (100 mg, 0.314 mmol), 2,4-dichloro-5-cyano- pyrimidine (81.9 mg, 0.471 mmol) and DIPEA (0.164 mL, 0.941 mmol) in rc-butanol (2 mL) was stirred at r.t. for 72 h. The mixture was dissolved in EtOAc (150 mL) and washed with saturated brine (3 x 30 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 97:2:1 DCM/ MeOH/NH3 solution in MeOH) gave an off-white glass (60 mg, 42percent). LCMS (ES+) 456 (M+H)+ (mixture of regioisomers). The off-white glass (60 mg, 0.132 mmol), 7M NH3 in MeOH (1.5 mL) and NH4OH (1 mL) were combined and heated under microwave irradiation at 1200C for 1 h. After addition of saturated brine (20 mL) the reaction mixture was extracted with EtOAc (3 x 60 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. Purification by preparative HPLC gave the title compounds (9.7 mg, 17percent; and 22.2 mg, 39percent) as white solids. deltaH (DMSO-de) 8.23 (IH, s), 8.01 (IH, s), 7.86 (IH, d, J 8.07 Hz), 7.73-7.64 (3H, m), 7.30-7.20 (IH, br s), 7.18 (2H, t, J7.76 Hz), 6.88 (IH, t, J5.30 Hz), 5.55-5.47 (IH, m), 3.98-3.92 (IH, m), 3.73-3.57 (2H, m), 2.22-1.96 (3H, m), 1.83-1.72 (IH, m), 1.63 (3H, d, J6.74 Hz). deltaH (DMSO-d6; T = 125°C) 8.23 (IH, s), 8.00 (IH, s), 7.65 (IH, s), 7.63 (IH, s), 7.45 (IH, d, J 8.00 Hz), 7.17 (IH, t, J 8.00 Hz), 7.09 (IH, br s), 6.70-6.57 (3H, m), 5.40-5.30 (IH, m), 4.02-3.95 (IH, m), 3.80-3.68 (2H, m), 2.25-2.10 (3H, m), 1.96-1.87 (IH, m), 1.63 (3H, d, J8.00 Hz). LCMS (ES+) 412 (M+H)+, 3.11 minutes {Method I). LCMS (ES+) 412 (M+H)+, 1.70 minutes {Method 2).

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 3177-24-0, 2,4-Dichloropyrimidine-5-carbonitrile.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BROWN, Julien, Alistair; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACDONALD, Jonathan, David; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; SHARPE, Andrew; WO2010/92340; (2010); A1;,
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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. 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below., COA of Formula: C5HCl2N3

Intermediate 14: Ethyl 3-[3-({[4-chloro-5-cyanopyrimidin-2-yllamino}methyl)-2- methylphenyllbenzoate:2,4-Dichloro-pyrimidine-5-carbonitrile (50 mg, 0.287 mmol, 1 .0 eq) was dissolved in DMF (1 ml) and intermediate 7 (77 mg, 0.287 mmol, 1.0 eq) was added to the solution, followed by DIEA (51 ul, 0.287 mmol, 1 .0 eq). The reaction mixture was stirred for 1 hour at room temperature, diluted with EtOAc (50 ml) and washed with water (50 ml x4). The organic fraction was dried over anhydrous Na2S04, filtrated and concentrated under reduced pressure and purified by preparative HPLC to yield the desired intermediate 14.

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, 3177-24-0, 2,4-Dichloropyrimidine-5-carbonitrile.

Reference:
Patent; AMAKEM NV; LEYSEN, Dirk; DEFERT, Olivier; BOLAND, Sandro; WO2012/156467; (2012); A1;,
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Reference of 3177-24-0, 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 3177-24-0 as follows.

To a cooled (-60 °C) solution of (lr,4r)-4-ethoxycyclohexanamine (6.82 g, 37.9 mmol) and 2,4-dichloropyrimidine-5-carbonitrile (6 g, 34.5 mmol) in THF (115 mL) was added DIEA (15.02 mL, 86 mmol) dropwise. The resulting mixture was stirred at -60 °C for 1 h and then allowed to warm to room temperature overnight. The resulting mixture was concentrated and the residue was purified by silica gel column- 125 -ATI-2514175vl chromatography (14 percent ethyl acetate in petroleum ether). The product fractions were combined and concentrated to afford 2-chloro-4-((lr,4r)-4-ethoxycyclohexylamino)- pyrimidine-5-carbonitrile (3.33 g, 11.86 mmol, 34.4 percent yield) and 4-chloro-2-((lr,4r)-4- ethoxycyclohexylamino)pyrimidine-5-carbonitrile (5.5 g, 19.59 mmol, 56.8 percent yield;1H NMR (400 MHz, DMSO-d6) delta ppm 8.62 – 8.87 (m, 2 H), 3.61 – 3.86 (m, 1 H), 3.44 (dd, J=7.03, 2.34 Hz, 2 H), 3.12 – 3.26 (m, 1 H), 1.75 – 2.15 (m, 4 H), 1.13 – 1.44 (m, 4 H), 1.08 (td, J=6.93, 1.76 Hz, 3 H); MS (ESI) m/z 281.1 [M+l]+) as white solids. Theregiochemistry of the major isomer was confirmed by comparison with the proton spectra of 4-chloro-2-((lr,4r)-4-methoxycyclohexylamino)pyrimidine-5-carbonitrile (synthesis described herein).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3177-24-0, its application will become more common.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
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Electric Literature of 3177-24-0, 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. 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile, molecular formula is C5HCl2N3, 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: DIPEA (0.86mmol) was added to the solution of 2,4-dichloropyrimidine-5-carnonitrile (0.57mmol) in DMF (0.5ml) and stirred at room temperature for 10min. A solution of aminobenzene reagent corresponding to desired product (0.57mmol) in DMF (0.5ml) was added dropwise to the reaction mixture and stirred for 1h. The resultant was evaporated under vacuum and extracted with EtOAc. The organic layer was collected, washed with brine, dried over MgSO4, filtered, and dried under reduced pressure. 4c was obtained from the reaction of 4b, whereby substitution at the 2-position occurred.

According to the analysis of related databases, 3177-24-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Phuangsawai, Oraphan; Beswick, Paul; Ratanabunyong, Siriluk; Tabtimmai, Lueacha; Suphakun, Praphasri; Obounchoey, Phongphat; Srisook, Pimonwan; Horata, Natharinee; Chuckowree, Irina; Hannongbua, Supa; Ward, Simon E.; Choowongkomon, Kiattawee; Gleeson, M. Paul; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 896 – 905;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3177-24-0, 2,4-Dichloropyrimidine-5-carbonitrile, 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, 3177-24-0, blongs to pyrimidines compound. name: 2,4-Dichloropyrimidine-5-carbonitrile

[00607] General conditions for the preparation of 2-amino-4-chloropyrimidine-5-carbonitrile:[00608] To a solution of 2,4-dichloropyrimidine-5-carbonitrile (E-1) (2.0 g, 11.5 mmol) in 1,4-dioxane (20 mL) at 0 °C, ammonium hydroxide (28-30percent, 4.4 mL, 34.5 mmol) is added dropwise, and the resulting mixture is stirred while warming from 0 °C to RT for 2 h. Then, the mixture is partitioned between ethyl acetate (200 mL) and water (50 mL). The organic layer is washed with brine, dried over Na2SO4 and filtered. The filtrate is mixed with silica gel and then concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0- 100percent ethyl acetate/hexanes to afford the product (E-2) (917 mg) and a mixture of (E-2) and (E-3). Additional (E-3) can be obtained from this mixture by a second column chromatographic purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3177-24-0, its application will become more common.

Reference:
Patent; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo, C.; EVANS, Catherine, A.; WO2015/168079; (2015); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile, the common compound, a new synthetic route is introduced below. Safety of 2,4-Dichloropyrimidine-5-carbonitrile

Example 20. Synthesis of 2-({[3′-(aminomethyl)-2-methyIbiphenyl-3- yIJmethyl}amino)-4-(4,5,7,8-tetrahydroimidazol4,5-dlazepn-6(lH)-yl)pyrmicline-5- carbonitrile; To a solution of (3′-aminomethyl-2′-methyl-biphenyl-3-ylmethyl)-carbamic acid tert-butyl ester (281 mg, 0.86 mmol) and diisopropylethylamine (0.165 mL, 0.95 mmol) in dichloromethane (5.0 mL) was added 2,4-dichloro-pyritnidine-5-carbonitrile (150 mg, 0.86 mmol). The ixn mixture was stirred at room temperature for 70 h, then adsorbed directly onto silica gel and purified by silica gel chromatography eluting with 20-45percent ethyl acetate in hcxancs to afford 254 mg of a colorless oil, identified as a 1:1 mixture of the desired product and the regioisomeric 4-addition product. This mixture was further purified by reverse phase semi-prep HPLC using 60percent acetonitrile/water (0.1percent TFA) as eluent to give 149 mg of {3′-[(4-chloro-5-cyano-pyrimidin-2-ylamino)-methyl]-2′-methyl-biphenyl-3- yhnethyl}-carbamic acid tert-butyl ester as an off-white solid, m/z 486.0 (M + Na)+.To a solution of l,4,5,6,7,8-hexahydro-imidazo[4,5-cyano-4-(4,5,7,8-tetrahydro-lH-imidazo[4,5-c?]azepin-6-yl)-pyrimidin-2-ylamino]- methyl}-2′-methyl-biphenyl-3-ylmethyl)-carbamic acid tert-butyl ester, m/z 565.1 (M + H)+.A solution of (3′-{[5-cyano-4-(4,5,7,8-tetrahydro-lH-imidazo[4,5-Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2007/76247; (2007); A1;,
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