Category: 591-55-9

Related Products of 591-55-9, 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. 591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, 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.

0387-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (100 mg), pyrimidine-5-amine (38 mg), tris(dibenzylideneacetone)dipalladium(0) (37 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (47 mg), cesium carbonate (267 mg), and 1,4-dioxane (2 mL) was stirred at 80 C. for 6 hours. The reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the obtained solution was purified by silica gel column chromatography (methanol-ethyl acetate), thereby obtaining 6-chloro-N-(pyrimidin-5-yl)-1,5-naphthyridine-3-amine (32 mg). MS m/z (M+H): 258.

According to the analysis of related databases, 591-55-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 591-55-9, 5-Aminopyrimidine, 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, 591-55-9, blongs to pyrimidines compound. Formula: C4H5N3

aminopyrimidine (2) (504mg, 5.0mmol), 2-chloropyrazine (1) (0.54mL, 6.0mmol), Pd2(dba)3 (138mg, 0.15mmol), XantPhos (175mg, 0.30mmol) and Cs2C03 (3.29g, 10.1 mmol) were added sequentially with continued degassing. The reaction mixture was degassed with Ar(g) for a further 10min then heated up to 90C overnight. Once cooled down to rt, it was poured into H20 (25ml_) and extracted with EtOAc (3 x 35ml_). The combined organic extracts were dried over MgS04, filtered, concentrated in vacuo and purified by silica gel column chromatography with CH2CI2/MeOH (1 :0-12: 1 ). The residue was re-dissolved in CH2CI2/MeOH (4: 1 , 50ml_) and swirled with MP-TMT resin (1.2g, 1.3mmol/g) at rt overnight. The solution was filtered, the resin washed with CH2CI2/MeOH (4:1 , 100ml_) and the filtrate concentrated in vacuo. Purification by silica gel column chromatography with EtOAc/MeOH (1 :0-16:1 ) then reverse-phase column chromatography with H20/MeCN (1 :0-9: 1 ) yielded (3) as an off-white solid (66mg, 8%). (0709) LCMS (ES): Found 174.1 [M+Hf.1H NMR (300 MHz, DMSO-cf6), d: 9.13 (s, 2H), 8.77 (s, 1 H), 8.30 (d, J=1.3 Hz, 1 H), 8.20 (dd, J= 2.8, 1.3 Hz, 1 H), 8.04 (d, J= 2.8 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,591-55-9, its application will become more common.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 591-55-9 as follows., 591-55-9

REFERENCE EXAMPLE 8 To 7 ml of dimethyl sulfoxide was added 0.69 g (6.15 mmol) of potassium tert-butoxide, and 468 mg (4.92 mmol) of 5-aminopyrimidine was added to the solution while cooling with water. After stirring at room temperature for 1 hour, 500 mg (2.46 mmol) of 2-bromo-5-nitropyridine was added thereto under cooling with water, followed by further stirring at room temperature for 30 minutes. The reaction solution was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid, and the washing was adjusted to pH 8.5 with a 1 N sodium hydroxide aqueous solution and again extracted with ethyl acetate. The organic layer was combined with the above obtained organic layer, washed successively with water and a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography (eluding solvent: chloroform-methanol). The resulting crude crystals were washed with ethyl ether to obtain 0.32 g (1.47 mmol) of 5-[N-(5-nitro-2-pyridyl)amino]pyrimidine. Mass Spectrum (m/z): 216 (M-H)+ NMR Spectrum (DMSO-d6, TMS internal standard) delta: 7.00 (1 H, d, J=9 Hz), 8.39 (1 H, dd, J=9 Hz, 3 Hz), 8.87 (1 H, s), 9.09 (1 H, d, J=3 Hz), 9.17 (2 H, s), 10.41 (1 H, s)

The chemical industry reduces the impact on the environment during synthesis 591-55-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5538976; (1996); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 591-55-9 as follows., 591-55-9

Example 4 3-Cyclopentyl-3-(4-(2-(pyrimidin-5-ylamino)thieno[3,2-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)propanenitrile T-04 Synthetic Route Preparation of Compound T-04 To a solution of compound 3 (50 mg, 0.14 mmol) and 5-aminopyrimidine (40 mg, 0.42 mmol) in isobutanol (0.5 mL) was added p-toluene sulfonic acid monohydrate (53 mg, 0.28 mmol). The mixture was heated to 110 C. and stirred for 16 hours. The mixture was then concentrated in vacuum and the residue was purified by preparation HPLC (mobile phase:acetonitrile, water (0.05% trifluoroacetic acid); gradient: 60%-90%-10%) to give compound T-04 (7 mg, yield: 12%) as a yellow solid. LC-MS (ESI): m/z=417 [M+H]+.1H-NMR (400 MHz, CD3OD) delta: 9.37 (s, 2H), 8.76 (s, 1H), 8.65 (s, 1H), 8.41 (s, 1H), 8.21 (d, J=6 Hz, 1H), 7.43 (d, J=6 Hz, 1H), 4.53 (m, 1H), 3.123.28 (m, 2H), 2.56 (m, 1H), 1.97 (m, 1H), 1.411.72 (m, 7H) ppm

The chemical industry reduces the impact on the environment during synthesis 591-55-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SHANGHAI CHEMEXPLORER CO., LTD.; XU, Zusheng; ZHANG, Nong; SUN, Qingrui; WANG, Tinghan; US2015/336982; (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 591-55-9, name is 5-Aminopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. 591-55-9

To a solution of (9S)-2-(2-(trifluoromethyl)pyridin-4-yl)-7,8,9,10-tetrahydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine (0.5 g, 1.561 mmol), triethylamine (0.653 mL, 4.68 mmol) in THF (10 mL) was added bis(trichloromethyl) carbonate (0.232 g, 0.780 mmol) at 25 C. under nitrogen atmosphere and stirred at RT for 30 min. Then pyrimidin-5-amine (0.445 g, 4.68 mmol) was added and heated the reaction mixture at 65 C. for 16 h. Allowed to cool to RT and solvent was removed on rota-vapour, the crude was diluted with CH2Cl2 (20 ml) and washed with water (5 ml), brine solution (5 ml) followed by dried over sodium sulfate. The organic solvent was evaporated under reduced pressure to obtain the crude product. The crude mixture was purified by prep-HPLC (formic acid, ACN 25%) to afford (9S)-N-(pyrimidin-5-yl)-2-(2-(trifluoromethyl)pyridin-4-yl)-8,9-dihydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine-10(7H)-carboxamide (250 mg, 0.56 mmol, 45% yield) as an off white solid (TLC: 80% EtOAc in Hexane, Rf: 0.5), LCMS (m/z): 442.3 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 13.07 (s, 1H), 9.08-8.72 (m, 4H), 8.38 (dd, J=1.7, 0.9 Hz, 1H), 8.28 (dd, J=5.2, 1.6 Hz, 1H), 7.90 (d, J=8.0 Hz, 1H), 7.79 (d, J=8.0 Hz, 1H), 4.85 (t, J=2.7 Hz, 1H), 3.43 (dd, J=13.7, 1.9 Hz, 1H), 3.33 (d, J=10.1 Hz, 2H), 2.91 (d, J=13.7 Hz, 1H), 2.15-1.79 (m, 2H), 1.33 (s, 2H).

Statistics shows that 591-55-9 is playing an increasingly important role. we look forward to future research findings about 5-Aminopyrimidine.

Reference:
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

591-55-9, 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.591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, molecular weight is 95.1, as common compound, the synthetic route is as follows.

REFERENCE EXAMPLE 10 To 5 ml of dimethyl sulfoxide (DMSO) containing 0.34 g of potassium tert-butoxide was added 0.29 g of 5-aminopyrimidine, followed by stirring at room temperature for about 15 minutes. To the reaction mixture was added dropwise 1 ml of a DMSO solution containing 0.33 g of p-fluorobenzotrifluoride, followed by heating at 60 C. for about 40 minutes. The reaction mixture was allowed to cool and poured into 150 ml of ice-water. The thus formed white crystals were collected by filtration and dried to obtain 0.17 g of 5-(4-trifluoromethylphenyl)aminopyrimidine. Mass Spectrum (m/z): 239 (M+) NMR Spectrum (DMSO-d6, TMS internal standard) delta: 7.25 (2 H, d, J=8 Hz), 7.59 (2 H, d, J=8 Hz), 8.68 (2 H, s), 8.77 (1 H, s), 9.02 (1 H, s)

Statistics shows that 591-55-9 is playing an increasingly important role. we look forward to future research findings about 5-Aminopyrimidine.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5538976; (1996); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

591-55-9, 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. 591-55-9, name is 5-Aminopyrimidine. A new synthetic method of this compound is introduced below.

To a solution of pyrimidin-5-amine (95.1 mg, 1.00 mmol) and N,N-diisopropylethylamine (175 mg, 1.35 mmol) in tetrahydrofuran (3 mL) at room temperature, was added a solution of ditrichloromethyl carbonate (101 mg, 0.34 mmol) in THF (3 mL) dropwise. After stirring for 15 min, triethylamine (152 mg, 1.50 mmol) and 1-[3-amino-4-[bis(2-methylpropyl)amino]phenyl]cyclobutane-1-carboxylic acid (80 mg, 0.25 mmol) was added. The resulting mixture was stirred at room temperature for another 2 h. The reaction was then concentrated under vacuum. The residue was purified by Prep-HPLC with the following conditions: [Column: X bridge, C18, 19*50mm; Mobile Phase, H2O (0.05% NH4HCO3)/MeCN, 35% – 55% in 8 min; Rate: 25 mL/ min; Detector, 254 nm] to afford the desired product (72.7 mg, 17% yield) of as a white solid. LCMS (ES, m/z): 440.5 [M+H]+. 1H NMR (300 MHz, DMSO-d6, ppm): delta 10.01 (s, 1 H), 8.93 (s, 2 H), 8.81 (s, 1H), 8.20 (s, 1H), 7.90 (d, = 2.1 Hz, 1 H), 7.19 (d, J= 8.3 Hz, 1 H), 6.92 (dd, J= 8.3, 2.2 Hz, 1 H), 2.68 (d, J= 6.9 Hz, 6 H), 2.42-2.26 (m, 2 H), 1.94-1.50 (m, 4 H), 0.86 (d, J= 6.5 Hz, 12 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. 591-55-9, 5-Aminopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INVENTISBIO INC.; DAI, Xing; WANG, Yaolin; (187 pag.)WO2017/139414; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

591-55-9 , The common heterocyclic compound, 591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, 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.

A solution of X-Phos (0.04 equiv) and Pd2(dba)3 (0.02 equiv) in toluene (15 vol) was bubbled with nitrogen and heated to 60 C for 15 min. (2S,4R)-1-(2-(3-Acetyl-5-bromo-1H-indol-1-yl)acetyl)-4-fluoro-N-phenethylpyrrolidine-2-carboxamide(1.2 equiv) and sodium tert-butoxide (1.4 equiv) was added to the reaction mixture and the reaction mixture was heated to 100 C for 16 h. After completion of the reaction, the reaction mixture was quenched with water. The resulting mixture was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous Na2S04, filtered and then concentrated. The residue was purified by column chromatography on silica gel using DCM/MeOH to give (2S,4R)-l-(2-(3- acetyl-5-(pyrimidin-5-ylamino)-lH-indol-l-yl)acetyl)-4-fluoro-N-phenethylpyrrolidine-2- carboxamide. NMR (400 MHz, DMSO-ifc) delta 8.56 (s, 1H), 8.49 – 8.47 (m, 3H), 8.23 (s, 1H), 8.19 – 8.12 (m, 1H), 8.01 (s, 1H), 7.43 (d, J = 8.8 Hz, 1H), 7.27 – 7.09 (m, 5H), 5.50 – 5.31 (m, 2H), 5.15 (d, J= 17.2 Hz, 1H), 4.35 – 4.31 (m, 1H), 4.19 – 3.85 (m, 2H), 3.56 – 3.40 (m, 1H), 3.24 – 3.13 (m, 1H), 2.72 – 2.66 (m, 2H), 2.41 (s, 3H), 2.41 – 2.33 (m, 1H), 2.01 – 1.98 (m, 1H).

According to the analysis of related databases, 591-55-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (319 pag.)WO2017/35351; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

591-55-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 591-55-9, name is 5-Aminopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 5-aminopyrimidine (CAS No. 591-55-9) (2.00 g, 21.0 mmol, 1 equivalent), triethylamine (14.7 mL, 105 mmol, 5 equivalents), EDC (7.26 g, 37.9 mmol, 1.8 equivalents), N,N-dimethyl-4-aminopyridine (0.257 g, 2.10 mmol, 0.1 equivalents) and DCM (60.0 mL) was added dropwise 3-(t-butoxy)-3-oxopropionic acid (CAS No. 40052-13-9) (4.86 mL, 31.5 mmol, 1.5 equivalents), and the mixture was stirred at room temperature for 3 days. To the reaction mixture were added water and ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (silica gel, 25%-71% ethyl acetate/n-heptane) to afford the title compound (4.73 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 1.52 (s, 9H), 3.44 (s, 2H), 8.98 (s, 1H), 9.03 (s, 2H), 9.77 (br. s, 1H).

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 591-55-9, 5-Aminopyrimidine.

Reference:
Patent; Eisai R&D Management Co., Ltd.; Kurokawa, Toshiki; Yoshida, Yu; Shin, Kogyoku; Kobayashi, Yoshihisa; Fukumoto, Hironori; Takeda, Kunitoshi; Ohashi, Yoshiaki; Kotake, Makoto; Shibuguchi, Tomoyuki; Watanabe, Toru; Kita, Yoichi; Hirota, Shinsuke; Fukuyama, Takashi; Kamada, Yasuaki; (59 pag.)US2017/137436; (2017); 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. 591-55-9, name is 5-Aminopyrimidine. A new synthetic method of this compound is introduced below., 591-55-9

General procedure: Ethyl 2-[(2-fluorophenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate. Diethyl malonate (1.0 mL, 6.6 mmol) was addeddropwise to a solution of sodium hydride (60% w/w in oil, 317 mg,7.9 mmol) in anhydrous tetrahydrofuran (12 mL) that was cooledwith ice bath. The mixture was heated at reflux for 6 min. Aftercooling with ice bath, the reaction mixture was treated dropwisewith chloroacetyl chloride (0.58 mL, 7.2 mmol) and stirred in the icebath for 1 h, and then stirred at 45 C for 1 h. The reaction mixturewas cooled in the ice bath again, and then 2-fluoroaniline (0.76 mL,7.9 mmol) was added dropwise. After stirring at ambient temperaturefor 17 h, the reaction mixture was heated at reflux for 2.5 h.The reaction mixture was allowed to cool to ambient temperature,diluted with aqueous saturated sodium bicarbonate solution, andextracted with ethyl acetate twice and with chloroform. Theorganic layerwaswashed with brine, dried over sodium sulfate andconcentrated. The residue was triturated with ethanol-hexane toafford the title compound as a pale yellow solid (0.58 g, 33%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,591-55-9, 5-Aminopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Irie, Takayuki; Asami, Tokiko; Sawa, Ayako; Uno, Yuko; Hanada, Mitsuharu; Taniyama, Chika; Funakoshi, Yoko; Masai, Hisao; Sawa, Masaaki; European Journal of Medicinal Chemistry; vol. 130; (2017); p. 406 – 418;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia