Category: 5177-27-5

Reference of 5177-27-5, 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.5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, molecular weight is 163.9927, as common compound, the synthetic route is as follows.

5-amino-2,4-dichloropyrimidine (0.15 mol) was dissolved in anhydrous tetrahydrofuran (100 mL),Add triethylamine (30.4g, 0.3mol) dropwise to the reaction system with a constant pressure dropping funnel with stirring at room temperature.The mixed solution with tert-butylamine (21.9g, 0.3mol) was dripped, and the reaction system was transferred to a 100 C oil bath for 16h.TLC showed the reaction was complete. After cooling to room temperature, water (100 mL) was added.Extract with ethyl acetate (100 mL x 3) and combine the organic phases.The organic phase was washed with saturated sodium chloride water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.It was separated and purified by silica gel column chromatography to obtain a red-brown solid (21.0 g, yield 69.8%).

Statistics shows that 5177-27-5 is playing an increasingly important role. we look forward to future research findings about 5-Amino-2,4-dichloropyrimidine.

Reference:
Patent; Jiangnan University; Tang Chunlei; Zhang Qing; Hu Xiaoxia; Zhao Hui; Zhao Kuantao; Zhang Yue; Fan Weizheng; (16 pag.)CN110357885; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5177-27-5 , The common heterocyclic compound, 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, 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 mixture of 0.5 g (3.1 mmol) of 5-amino-2,4-dichloropyrimidine [D. T. Hurst, Heterocycl. 22, 79 (1984)], 0.35 ml (3.1 mmol) of 2-fluorobenzylamine and 0.46 ml (3.4 mmol) of triethylamine in 8 ml of 1-butanol is heated under reflux for 24 hours. The reaction mixture is then cooled to 0. The resulting beige-coloured suspension is filtered with suction and the filter cake is washed with cyclohexane and suspended in water for 30 minutes at room temperature with stirring. The suspension is again filtered with suction and the filter cake is dried under a high vacuum at 100 over tetraphosphorus decaoxide. In this manner 5-amino-2-chloro-4-[N-(2-fluorobenzyl)amino]-pyrimidine is obtained in the form of beige-coloured crystals having a melting range of from 224 to 225.

The synthetic route of 5177-27-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US5110818; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 5177-27-5, 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. 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, 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 round-bottomed flask equipped with a magnetic stirrer was added 2,4-dichloropyrimidin-5-amine (1.89 g, 11.52 mmol), DIPEA (8.05 ml, 46.1 mmol), morpholine-3-carboxylic acid (1.66 g, 12.68 mmol), and DMSO (5 ml). The reaction was stirred at 100 C. overnight. The reaction mixture was poured into water and extracted with EtOAc 3 times. The pH of the aqueous layer was adjusted (about 5) with 10% citric acid and extracted again with EtOAc. The combined organic layer dried over MgSO4, filtered, and concentrated in vacuo to furnish a tan solid. The solid was triturated in diethyl ether containing a small amount of EtOH, filtered, and dried to give 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one: 1.95 g (70.3%). MS [M+H] found 241.

According to the analysis of related databases, 5177-27-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2011/53921; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 5177-27-5, 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 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 2,4-dichloropyrimidin-5-amine (1.58 g, 9.63 mmol) and dihydro-2H-thiopyran-4(3H)-one (1.45 g, 12.5 mmol) in dichloromethane (50 ml) at 0 C. was added dropwise a 1 M solution of titanium tetrachloride (10.6 ml, 10.6 mmol) in dichloromethane. After the reaction mixture was stirred at room temperature for 2 h, sodium cyanoborohydride (1.91 g, 28.9 mmol) was added in single portion and the reaction mixture was stirred at room temperature for 16 hours. After the reaction mixture was diluted with dichloromethane, the reaction mixture was poured carefully into iced-saturated NaHCO3 solution. EtOAc was added and then the insoluble materials were filtered off. The phases of the filtrate were separated, and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with water and saturated NaCl, dried with Na2SO4 and concentrated in vacuo to give a crude oil. The crude residue was purified by silica gel chromatography (hexane/ethyl acetate, 100:0 to 3:1) to afford 2,4-dichloro-N-(tetrahydro-2H-thiopyran-4-yl)pyrimidin-5-amine (864 mg, 3.27 mmol, 34% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.59-1.76 (m, 2H) 2.07-2.20 (m, 2H) 2.58-2.69 (m, 2H) 2.70-2.85 (m, 2H) 3.42-3.57 (m, 1H) 5.78 (d, J=8.84 Hz, 1H) 8.25 (s, 1H). MS [M+H] 264.

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 5177-27-5, 5-Amino-2,4-dichloropyrimidine.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2011/53921; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5177-27-5, 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 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

5-Amino-2,4-dichloropyrimidine (1.33 g, 10 mmol) and 5-aminoindazole (1.64 g, 10 mmol) were slurried in a solution of sodium acetate (20 mL, 0.1 M buffered to pH 4 with acetic acid). The reaction mixture was then heated to 60-65 C for 16 hours at which point no starting materials remained by t.l.c. The reaction mixture was cooled and the precipitate filtered off washed with water (20 mL), saturated sodium bicarbonate solution (10 mL) and again with water (2×20 mL). The solid was dried under vacuum for 12 hours (2.00 g, 7.6 mmol, 76% Yield). 1H,400MHz, delta (d6-DMSO): 5.68 (3H, br s, NH), 7.52 (2H, s, ArH), 7.61 (IH, s, ArH), 8.05 (IH, s, ArH), 8.06 (IH, s, ArH), 9.09 (IH, s, NH); HPLC: 3.95 min; LRMS: m/z = 261.1 (M+H)

According to the analysis of related databases, 5177-27-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DCAM PHARMA INC; AJAMI, Alfred, M.; DUNCAN, Kenneth, W.; FANG, Xinqin; WO2011/106168; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Amino-2,4-dichloropyrimidine

To a round-bottomed flask equipped with a magnetic stirrer was added 2,4-dichloropyrimidin-5-amine B (1.89 g, 11.52 mmol), DIPEA (8.05 mL, 46.1 mmol), morpholine-3-carboxylic acid A (1.66 g, 12.68 mmol), and DMSO (5 mL). The reaction was stirred at 100oC overnight. The mixture was poured into water and extracted with EtOAc for three times. The pH of the aqueous layer was adjusted (about 5) with 10 percent citric acid and extracted again with EtOAc. The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo to furnish a tan solid. The solid was triturated in diethyl ether containing a small amount of EtOH, filtered, and dried to give 2-chloro-6a,7,9,10-tetrahydro -[1,4]oxazino[3,4-h]pteridin -6(5H)-one C: 1.95 g (70.3% yield). MS [M+H] found 241.

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, 5177-27-5, 5-Amino-2,4-dichloropyrimidine.

Reference:
Article; Jin, Stanley; Mikami, Satoshi; Scorah, Nick; Chen, Young; Halkowycz, Petro; Shi, Lihong; Kahana, Jason; Vincent, Patrick; de Jong, Ron; Atienza, Joy; Fabrey, Robyn; Zhang, Lilly; Lardy, Matthew; Bioorganic and Medicinal Chemistry Letters; vol. 29; 21; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5177-27-5, 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. 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, 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 2,4-dichloropyrimidin-5-amine (0.5 g, 3.04 mmol), sodium methoxide (0.66 g, 12.19 mmol) and methanol (10 ml) was refluxed for 16 hours. The solvent was removed under reduced pressure. Water was added and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 2-chloro-4-methoxypyrimidin-5-amine after flash chromatography (100-200 mesh size silica gel, 20-25% ethyl acetate in hexane) was 0.35 g. N-Bromosuccinimide (67 mg, 0.37 mmol) was added to a solution of 2-chloro-4-methoxypyrimidin-5-amine (50 mg, 0.31 mmol) in chloroform (2 ml) and the resulting mixture was stirred at RT for 3 hours. Water was added and the mixture extracted with chloroform. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 4-bromo-2-chloro-6-methoxypyrimidin-5-amine was 60 mg.

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 5177-27-5, 5-Amino-2,4-dichloropyrimidine.

Reference:
Patent; MEDEIA THERAPEUTICS LTD; RATILAINEN, Jari; GOLDSTEINS, Gundars; WO2014/191632; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5177-27-5, 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 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Tri(2-furyl)phosphine (36 mg, 0.16 mmol) and Pd2(dba)3 (20 mg, 0.020 mmol) were added to DMF (10 mL) under N2 at ambient temperature and stirred for 10 min. Subsequently, 2,4-dichloropyrimidine-5-amine (8d) (100 mg, 0.600 mmol) and (2-furyl)tributyltin (0.2 mL, 0.6 mmol) were added. The mixture was stirred at 60 C for 16 h, and evaporated in vacuo. The residue was dissolved in satd KF in THF (20 mL), stirred at ambient temperature for 16 h, and evaporated in vacuo. The residue was placed on top of a flash chromatography column and the product was purified by flash chromatography on silica gel eluting with EtOAc/CH2Cl2/hexane (5:8:12); yield 73 mg (61%), mp 169-170 C, yellow solid. 1H NMR (CDCl3, 500 MHz) delta 8.08 (s, 1H, H-4), 7.61 (dd, J=1.8, 0.7 Hz, 1H, H-5 in furyl), 7.31 (dd, J=3.6, 0.7 Hz, 1H, H-3 in furyl), 6.59 (dd, J=3.6, 1.8 Hz, 1H, H-4 in furyl), 4.71 (s, 2H, NH2); 13C NMR (CDCl3, 75 MHz) delta 152.4 (C-2 in furyl), 149.6 (C-2), 148.2 (C-4), 144.6 (C-5 in furyl), 141.3 (C-6), 135.1 (C-1), 113.9 (C-3 in furyl), 112.8 (C-4 in furyl); MS EI m/z (rel %) 197/195 (38/100, M+), 168 (19), 166 (49), 67 (3); HRMS (EI) calcd for C8H6ClN3O: 195.0199. Found 195.0197.

According to the analysis of related databases, 5177-27-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Read, Matthew L.; Krapp, Andreas; Miranda, Pedro O.; Gundersen, Lise-Lotte; Tetrahedron; vol. 68; 7; (2012); p. 1869 – 1885;,
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.5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, molecular weight is 163.9927, as common compound, the synthetic route is as follows.SDS of cas: 5177-27-5

To a mixture containing 2,4-dichloropyrimidin-5-amine (900 mg, 5 5 mmol), 4- ethynyl-l,2~dimethoxy benzene (980 mg, 6.0 mmol), copper(I) iodide (105 mg, 0 55 mmol) and Pd(Ph3P)4 (190 mg, 0 17 mmol) in a screw cap vial was added nitrogen gas purged TEA (15 mL). The vial was fitted with a Teflon lined septum cap. The system was evacuated under vacuum (via a needle from a mtrogen/vacuum manifold line) and backfilled with nitrogen gas. The needle was removed and the vial was heated at 100 C for 3 h. The reaction mixture was cooled to room temperature and concentrated. The resulting slurry was dissolved in THF/DCM/MeOH mixture and adsorbed to 10 g silica and transferred to an empty cartridge. The cartridge was fitted to a Teledyne ISCO CombiFlash Rf chromatography system and purified on a 24 g ISCO silica gel column which was eluted over a 15 min gradient with 5%-100% hexanes/EtOAc to afford 2- chloro-4-((3,4-dimethoxyphenyl)ethynyl)pyrimidin-5-amine (1.3 g, 4.5 mmol, 82 % yield), MS m/z (290, M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5177-27-5, 5-Amino-2,4-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; MUSSARI, Christopher P.; WHITELEY, Brian K.; KUMAR, Sreekantha Ratna; RAMACHANDRA REDDY, Anupama Kandhi; (134 pag.)WO2019/126083; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5177-27-5, 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 5177-27-5 as follows.

To 2,4-dichloro-pyrimidin-5-ylamine (3.03 g, 18.1 mmol)In n-BuOH (40 mL)(1S,2S)-2-Amino-cyclopentanol hydrochloride (2.50 g, 17.2 mmol) was added to the stirred suspensionAnd DIEA (9.20 mL, 51.8 mmol).The mixture was stirred at 130 C for 4 h.Then the reaction mixture under reduced pressure and EtOAc was concentrated and the crude product was triturated in the heptane and filtered to yield a solid BT-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5177-27-5, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BAKONYI,JOHANNA; BRUNETTE,STEVEN RICHARD; COLLIN,DELPHINE; HUGHES,ROBERT OWEN; LI,XIANG; LIANG,SHUANG; SIBLEY,ROBERT; TURNER,MICHAEL ROBERT; WU,LIFEN; ZHANG,QIANG; (169 pag.)TW2018/38997; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia