Pyrimidines

A common compound: 1820-81-1, name is 5-Chlorouracil,molecular formula is C4H3ClN2O2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 1820-81-1

Method 5 2,4,5-Trichloropyrimidine 5-Chlorouracil (10.0 g, 68.5 mmol) was dissolved in phosphorus oxychloride (60 ml) and phosphorus pentachloride (16.0 g, 77.0 mmol) was added. The mixture was heated under reflux for 16 hours, left to cool and then poured slowly into water (200 ml) with vigorous stirring. The mixture was stirred for 1.5 hours and then ethyl acetate (250 ml) was added. The organic layer was separated and the aqueous layer was extracted with a further portion of ethyl acetate (250 ml). The combined extracts were washed with saturated sodium bicarbonate (200 ml) and saturated sodium chloride solution (200 ml), and then dried. Volatile material was removed by evaporation and the residue was purified by column chromatography, eluding with DCM, to give the product as a yellow liquid (6.37 g, 51%). NMR (CDCl3): 8.62 (s, 1H); MS (MH+): 182, 184, 186.

With the rapid development of chemical substances, we look forward to future research findings about 1820-81-1.

Reference:
Patent; Pease, Elizabeth Janet; Breault, Gloria Anne; Bradbury, Robert Hugh; US2003/114473; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

156-81-0, 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 156-81-0, name is Pyrimidine-2,4-diamine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-bromo-1-(5-bromo-2,4-dimethoxyphenyl)ethanone 7 (62 mg, 0.0.21 mmol) and pyrimidine-2,4-diamine 164a (20 mg, 0.18 mmol) in acetone (5 ml) was heated to reflux for 3h. The reaction mixture was cooled to room temperature: the white precipitate was filtered and washed with acetone. The precipitate was suspended in aqueous ammonia (10 mL) and stirred for 30 mins. The precipitate was filtered, washed with water. The solid was converted to HCl salt by treating it to dilute HCl. The precipitate obtained dried under reduced pressure to yield 2-(5-bromo-2,4-dimethoxyphenyl)imidazo[l,2-a]pyrimidin-7-amine hydrochloride 164a (18 mg, 44%) as an off-white solid. 1H NMR (300 MHz, DMSO-ifc): delta 8.54- 8.52(d, ./ 7.6 Hz, 1H), 8.22 (br s, 2H), 8.11 (s, 1H), 8,07 (s, 1H), 6.92(s, 3H), 6,71-6.68(d, J= 7,6 Hz, 1H), 4.03 (s, 3H), 3 ,97 (s, 3H). HPLC (Method 3} 97.8% (AUC), = 16.84 min; APCI MS m/z 351 [M +2+ i l l .

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 156-81-0, Pyrimidine-2,4-diamine.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); 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 1004-40-6, name is 6-Amino-4-hydroxy-2-mercaptopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. 1004-40-6

Step two, the above 2-mercapto-4-amino-6-hydroxypyridine was added to aqueous ammonia, 2-mercapto-4-amino-6-hydroxypyridine and the mass ratio of 1:15 ammonia, the ammonia concentration was 25 %, and then adding the active nickel and titanium oxide, 2-mercapto-4-amino-6-hydroxypyridine, activated nickel, titanium dioxide molar ratio of these three is 1: 4: 1.5, was heated to 90 deg.] C, refluxed for 5 hours, then take advantage of The active nickel and titanium dioxide were removed by hot filtration, cooled to room temperature, and a solid precipitated. The solid was washed with 30 ml of water and dried at 40 C to give 4-amino-6-hydroxypyrimidine in a yield of 98.4%

Statistics shows that 1004-40-6 is playing an increasingly important role. we look forward to future research findings about 6-Amino-4-hydroxy-2-mercaptopyrimidine.

Reference:
Patent; Shanghai Titan Technology Co., Ltd; Xie, Yingbo; Zhang, Qing; Zhang, Hua; Xu, Xiaobing; Luo, Guiyun; (7 pag.)CN105218554; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

1193-24-4 ,Some common heterocyclic compound, 1193-24-4, molecular formula is C4H4N2O2, 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.

Example 7 (for comparison) 460 g of phosphorus oxychloride and 62 g of N,N-dimethylaniline were mixed and 116 g of 4,6-dihydroxypyrimidine (98% pure) were metered into the mixture with a screw at 100 C. in the course of 5 hours. Thereafter, the reaction mixture was subsequently stirred at 106 to 128 C. for 8 hours. It was diluted with 300 g of chlorobenzene and discharged onto 1.2 kg of ice. The organic phase was separated off, washed twice with 100 ml of water each time and then subjected to fractional distillation. 85.7 g of 4,6-dichloropyrimidine (=58% of theory) are thus obtained.

According to the analysis of related databases, 1193-24-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Aktiengesellschaft; US5719285; (1998); A;,
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.3934-20-1, name is 2,4-Dichloropyrimidine, molecular formula is C4H2Cl2N2, molecular weight is 148.9781, as common compound, the synthetic route is as follows.3934-20-1

General procedure: To a solution of absolute ethanol (5 mL) and dichlorodiazine (3.36 mmol) in a 50mL round-bottom flaskwas added triethylamine (5.03 mmol), followed by the amine (5.03 mmol). The mixture was stirred either under reflux of ethanol (for dichloropyridazine and for dichloropyrazine) or at room temperature (for dichloropyrimidines). The reaction was monitored by GC. Once the starting dichlorodiazinewas completely consumed, the mixture was poured into a saturated NH4Cl solution (20 mL), then extracted with CH2Cl2 (320 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated under vacuum. The crude solid was triturated in petroleum ether, filtered through a Buchner to afford the pure product.

Statistics shows that 3934-20-1 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloropyrimidine.

Reference:
Article; Sengmany, Stephane; Lebre, Julie; Le Gall, Ewan; Leonel, Eric; Tetrahedron; vol. 71; 29; (2015); p. 4859 – 4867;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

5750-76-5, 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.5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, molecular weight is 183.4231, as common compound, the synthetic route is as follows.

Intermediate 13: 2,5-Dichloro-4-methylpyrimidine.To a solution of 2 ,4,5-trichloropyrimidine (2.52 g, 13.74 mmol) in THF/NMP (86 mL/6 mL) was added Fe(acac)3 (485 mg, 1 .37) and the mixture was cooled to 0 C. 3.0 M MeMgBr in Et2O (6.87 mL, 20.61 mmol) was added dropwise. After 30 min at 0 C, the reaction was complete and quenched with saturated aqueous NH CI solution. Et2O was added and the layers were separated and the aqueous layer was further extracted with several portions of Et2O. The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (Hex to 10% EtOAc/Hex) gave the desired product as a white solid (1 .45 g, 65%). 1 H NMR (500 MHz, CDCI3): 8.47 (s, 1 H), 2.61 (s, 3H).

Statistics shows that 5750-76-5 is playing an increasingly important role. we look forward to future research findings about 2,4,5-Trichloropyrimidine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50202; (2011); 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. 5750-76-5, name is 2,4,5-Trichloropyrimidine. A new synthetic method of this compound is introduced below., 5750-76-5

2-(isopropylsulfonyl)aniline (1g, 5.02mmol) and 2,4,5-trichloropyrimidine (1.1g, 6mmol) was dissolved in N,N-dimethylformamide (30 mL) and added sodium hydride (content 60%, 0.4g, 10mmol) then reacted at 25C for 12 hours. Water (20mL) was added then extracted with ethyl acetate (30mL ¡Á 3). The organic phases were combined, washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 25: 1) gave the product (0.8g, 46% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5750-76-5, 2,4,5-Trichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Shandong Xuanzhu Pharma Co., Ltd.; Wu, Yongqian; (28 pag.)CN105524045; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

302964-08-5, 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. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide. A new synthetic method of this compound is introduced below.

N-(2-chloro-6-methylphenyl)-2-(2-methyl-4,5′-bipyrimidin-6-ylamino)thiazole-5- carboxamideTo 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6- methylphenyl)thiazole-5-carboxamide (250 mg, 0.634 mmol) in dioxane (10 mL) was added pyrimidin-5-ylboronic acid (94 mg, 0.759 mmol), PdCl2(PPh3)2 (89 mg, 0.127 mmol) and Na2CO3 (2 M, 1 mL, 1.902 mmol). The mixture was stirred under Argon overnight in an oil bath (12O0C). The reaction mixture was cooled to room temperature and water was added, extracted with 10% MeOH in CHCl3 (3×50 mL). The organic layers were washed with brine and dried over anhydrous Na2SO4. The solvent was removed and the crude was purified with preparative HPLC (ACN/ 0.1 % TFA in water) to obtain the title compound as a yellow solid (180 mg, 52%). 1H-NMR (400 MHz, d6-DMSO) delta 12.31 (br s, IH), 10.02 (s, IH), 9.36 (s, 2H), 9.35 (s, IH), 8.34 (s, IH), 7.43 (s, IH), 7.41 (d, J= 1.6 Hz, IH), 7.32-7.25 (m, 2H), 2.71 (s, 3H), 2.26 (s, 3H); MS (m/z): 438.2 [M+l]+.

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. 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LIANG, Congxin; KOENIG, Marcel; HE, Yuanjun; WO2008/150446; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Some common heterocyclic compound, 137234-74-3, molecular formula is C6H6ClFN2, 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.137234-74-3

In a 500 mL three-necked flask, 150 mL of dichloroethane was added, 34.1 g of the chlorinated product prepared in the same manner as in the above step (3)1.5 g of azobisisobutyronitrile(AIBN) 28.4 g of N-bromosuccinimide(NBS) was dissolved in 50 mL of dichloroethane, Then drop into the reaction bottle, add dichloroethane 50mL. After the reaction solution was clarified, a mixed solution of 22.1 g of NBS dissolved in 100 mL of dichloroethane was added dropwise, and the mixture was heated to 50 C and reacted for 15 h. After the completion of the reaction, 100 mL of water was added to separate the aqueous phase and the organic phase. The aqueous phase was extracted with 80 mL of dichloroethane and the organic layers were combined. The organic layer was washed with sodium bisulfite solution and the organic layer was washed with water The organic layer was dried over anhydrous sodium sulfate,The solvent dichloroethane was distilled off under reduced pressure to obtain 52.6 g of the target compound 4-(1-bromoethyl)-5-fluoro-6-chloropyrimidine as a pale yellow liquid in a yield of 92%, and the purity of the high performance liquid chromatography was 86% .

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 137234-74-3.

Reference:
Patent; JUHUA Group Technology Center; YANG, JIANRONG; GE, CHENGSHENG; LI, JIAN; (8 pag.)CN103896855; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

156-81-0, 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 156-81-0 as follows.

2-(3-Fluoro-phenyl)-imidazo[1,2-a]pyrimidin-7-ylamine 2-Bromo-1-(3-fluorophenyl)ethanone (10.9 g, 50 mmol) was added to a solution of 2,4-diaminopyrimidine (3.70 g, 34 mmol) in acetone (185 ml), and the mixture was heated to reflux for 6 h. The cooled suspension was filtered and the precipitate was washed with acetone (50 ml). The solid was re-suspended in water (35 ml) and NH4OHaq. (25%, 50 ml), then it was collected over a glass fiber paper and the filtrate was washed with H2O (75 ml). After drying under vacuum, the product was obtained (5.56 g, 72%) as a yellow solid. MS (m/z)=229.1 [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,156-81-0, its application will become more common.

Reference:
Patent; Alvarez Sanchez, Ruben; Bleicher, Konrad; Flohr, Alexander; Gobbi, Luca; Groebke Zbinden, Katrin; Koerner, Matthias; Kuhn, Bernd; Peters, Jens-Uwe; Rudolph, Markus; US2011/237564; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia