Pyrimidines

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. 208465-21-8, name is Mesosulfuron-methyl. This compound has unique chemical properties. The synthetic route is as follows. 208465-21-8

Example 25 – 1-(4,6-Dimethoxypyrimidin-2-yl)-3-[2-(hydroxymethyl)-5- (methanesulfonamidomethyl henyl]sulfonyl-urea 8 To a solution of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4- (methanesulfonamidomethyl)benzoate (2 g, 3.98 mmol) in THF (30 mL) was added lithium aluminium hydride (755 mg, 19.88 mmol), portionwise, at -20 C. The reaction mixture was warmed to ambient temperature over 1 h, after which time TLC showed complete consumption of the starting material. The reaction was quenched with IPA (5 mL), MeOH (5 mL) and H20 and then acidified to pH 3 with 2 M HCI before being extracted with EtOAc, the organic layer dried over MgS04 and the solvent removed in vacuo. The resulting product was purified by flash chromatography on silica gel (solvent EtOAc) to afford the desired product as a white solid (1.12 g, 59%). 1 H NMR deltaEta (CDCIs, 300 MHz): 9.11 (s, 1 H), 7.90 (s, 1 H), 7.53 – 7.51 (m, 1 H), 7.40 – 7.38 (m, 1 H), 7.24 – 7.20 (m, 1 H), 5.51 (s, 1 H), 4.75 (s, 2H), 4.06 (d, J = 6.0 Hz, 2H), 3.70 (s, 6H), 2.60 (br, 2 H), 2.56, (s 3H). ESI-MS 476.1 [MH]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,208465-21-8, Mesosulfuron-methyl, and friends who are interested can also refer to it.

Reference:
Patent; REDX PHARMA LIMITED; THOMPSON, William; JACKSON, Peter; LINDSAY, Derek; SCREEN, Thomas; MOLTON, Benjamin; URCH, Christopher; WO2013/136073; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

591-55-9, A common compound: 591-55-9, name is 5-Aminopyrimidine,molecular formula is C4H5N3, 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.

REFERENCE EXAMPLE 9 To 10 ml of dimethyl sulfoxide was added 1.40 g (12.5 mmol) of potassium tert-butoxide, and to the solution was added 951 mg (10.0 mmol) of 5-aminopyrimidine while cooling with water. After stirring at room temperature for 1 hour, 0.54 ml (5.0 mmol) of 2-fluorobenzonitrile was added thereto while cooling with water, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into ice-water, and the mixture was adjusted to pH 7.0 with 1 N hydrochloric acid, and filtered. The filter residue was dissolved in 200 ml of acetone, and the acetone solution was filtered. The filtrate was dried over magnesium sulfate, and the solvent was removed by distillation under reduced pressure to obtain 0.53 g (2.70 mmol) of 5-[N-(2cyanophenyl)amino]pyrimidine. Mass Spectrum (m/z): 196 (M+) NMR Spectrum (DMSO-d6, TMS internal standard) delta: 7.12 (1 H, t, J=7 Hz), 7.35 (1 H, d, J=8 Hz), 7.57-7.60 (1 H, m), 7.76 (1 H, dd, J=8 Hz, 1 Hz), 8.61 (2 H, s), 8.78 (1 H, s), 8.84 (1 H, s)

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 591-55-9.

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

932-52-5, 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 932-52-5, name is 5-Aminopyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

Example 26-methylpyrido[3,2-d]pyrimidine-2,4(1H,3H)-dione 2 Into a 2000-mL 4-necked round-bottom flask was placed a solution of 5-aminopyrimidine-2,4(1H,3H)-dione 1 (217 g, 1.71 mol, 1.00 equiv) in HCl (20%, 1302 mL), then added (E)-but-2-enal (143.5 g, 2.05 mol, 1.20 equiv). The resulting solution was heated to reflux for 3 h (hours) in an oil bath. The reaction mixture was cooled and filtered. The filtrate was concentrated under vacuum. The residual solution was diluted with 250 mL of water and adjusted to pH 10 with ammonia (25%). The isolated solid was collected by filtration, then washed with 2¡Á100 mL of water, 2¡Á250 ml of ethanol and 3¡Á500 mL of ether and finally dried in an oven. This resulted in 63 g (21%) of 6-methylpyrido[3,2-d]pyrimidine-2,4(1H,3H)-dione 2. 1H-NMR (400 MHz, CD3OD, ppm): 7.56 (2H, s), 2.60 (3H, s)

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 932-52-5, 5-Aminopyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; Castanedo, Georgette; Chan, Bryan; Lucas, Matthew C.; Safina, Brian; Sutherlin, Daniel P.; Sweeney, Zachary; US2011/207713; (2011); 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. 3934-20-1, name is 2,4-Dichloropyrimidine, molecular formula is C4H2Cl2N2, 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. 3934-20-1

56.8g (381mmol) 2,4-dichloropyrimidine was dissolved in 500ml of ethylene glycol dimethyl ether (0 leg), 50.1g (381mmol) of anhydrous AlCl3 was added under N2 protection conditions, stirred for 5min, added 50g (381mmol) of intermediate 2, heated to 80 CStir for 3 h. After the reaction was completed, it was cooled to room temperature, and the above mixed solution was added dropwise to 500 mL of vigorously stirred water, stirred at room temperature for 3 hours, and suction filtered to give a dark red solid. The filter cake was washed with water and methanol until the filter cake turned white and dried. 65. 1g of white solid, yield 70.1%,

The chemical industry reduces the impact on the environment during synthesis 3934-20-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Jiangxi Science and Technology Normal University; Zhu Wufu; Zheng Pengwu; Zhao Bingbing; Xu Shan; Xiao Zhen; Hu Xiaohan; Zhou Zhihui; He Jie; Lai Luogen; Yang Qi; Tian Fajuan; (31 pag.)CN109280048; (2019); A;,
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. 90213-66-4, name is 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3Cl2N3, 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. 90213-66-4

To a mixture of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (1.67 g, 8.88 mmol), p- toluenesulfonyl chloride (1.72 g, 9.02 mmol) and triethylamine (2.50 mL, 18.0 mmol) in CH2C2 (15 mL), dimethylaminopyridine (30 mg, 0.24 mmol) was added. It was stirred at room temperature for 20 h. Water and CH2Ci2 were added. The organic phase was separated, washed with IN HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 2,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine as a solid (3.03 g).

The chemical industry reduces the impact on the environment during synthesis 90213-66-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; WO2009/131687; (2009); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

49845-33-2 , The common heterocyclic compound, 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine, molecular formula is C4HCl2N3O2, 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.

Isopropylamine(4.5ml) and N,N-diisopropylethylamine(13.2ml) were dissolved into 150ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitropyrimidine(10.0g) in dichloromethane(30ml) at 0¡ãC. After the completion of the dropwise addition, the mixture was kept at the same temperature to react for half an hour. Purification was conducted by a column chromatography to obtain a bright-yellow solid(10.1g) in a yield of 90.4percent.?1H NMR(400 MHz, CDCl3): delta 9.03(s, 1H), 8.24(s, 1H), 4.53(m, 1H), 1.34(d, J=6.8Hz, 6H)ppm.

According to the analysis of related databases, 49845-33-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Si Chuan University; CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; YANG, Shengyong; WEI, Yuquan; EP2578584; (2013); 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 32779-36-5, name is 5-Bromo-2-chloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. 32779-36-5

To 1,4-dioxane (30 mL) were added tert-butyl piperazine-1-carboxylate (2.89 g, 15.51 mmol), 5-bromo-2-chloropyrimidine (2.00 g, 10.34 mmol) and potassium carbonate (2.86 g, 20.68 mmol) sequentially. The mixture was heated to 110 ¡ãC, after stirring for 12 hours, the reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (3.15 g, 88.7percent).MS (ESI, pos. ion)m/z: 343.1 [M+H] and?HNMR(400IVIHz, CDC13): (ppm) 8.29 (s, 2H), 3.83-3.66 (m, 4H), 3.56-3.41 (m, 4H), 1.48 (s, 9H).

Statistics shows that 32779-36-5 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-chloropyrimidine.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; LIANG, Haiping; YI, Chao; ZHANG, Ji; (94 pag.)WO2016/192657; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

1820-81-1, 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. 1820-81-1, name is 5-Chlorouracil. A new synthetic method of this compound is introduced below.

General procedure: A mixture of commercially available beta-d-ribose tetraacetate (6.28 mmol) with pyrimidine base (8.8 mmol), 30.8 mL of acetonitrile, hexamethyldisilazane (10.9 mmol, 1.24 equiv), saccharine (0.4 mmol, 0.046 equiv) and trimethylsilyl trifluoromethane-sulfonate (8.8 mmol, 1.4 equiv) was taken in a Erlenmeyer flask. The Erlenmeyer flask was placed in a microwave oven and irradiated under at low power (100 W) for 3 min. The reaction mixture was cooled at room temperature, neutralized with aqueous sodium bicarbonate, and extracted with CH2Cl2. The organic extract was dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The residue was purified by column chromatography eluting with AcOEt/hexane 7:3, resulting in the desired nucleosides 5a-e, in 75-82% yields. Finally, the protected nucleosides 5a-e (1 mmol) were treated with ammonia/MeOH (saturated at 0 C, 41.8 mL) overnight at room temperature. The solvent was evaporated under reduced pressure to give compounds 6a-e, in 85-92% yields. Chemical and physical properties of the ribofuranosyl nucleosides were in agreement with previous data.31-35

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1820-81-1, 5-Chlorouracil, and friends who are interested can also refer to it.

Reference:
Article; Parmenopoulou, Vanessa; Chatzileontiadou, Demetra S.M.; Manta, Stella; Bougiatioti, Stamatina; Maragozidis, Panagiotis; Gkaragkouni, Dimitra-Niki; Kaffesaki, Eleni; Kantsadi, Anastassia L.; Skamnaki, Vassiliki T.; Zographos, Spyridon E.; Zounpoulakis, Panagiotis; Balatsos, Nikolaos A.A.; Komiotis, Dimitris; Leonidas, Demetres D.; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7184 – 7193;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

137234-74-3, 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. 137234-74-3, name is 4-Chloro-6-ethyl-5-fluoropyrimidine. A new synthetic method of this compound is introduced below.

Preparation of 4-(4-chloro-phenylsulfanyi)-6-ethyI-5- flu oropy rimidin e 61.O g of 4-chloro-6-ethyl-5-fluoropyrimidine was added to 600 mNo. of acetonitrile, and 60.4 g of 4-chlorothiophenol was added thereto followed by lowering the temperature to 10 C . 66.1 mi of diisopropylethylamine was added to the resulting solution, and reacted for 2 hours while maintaining the temperature at room temperature. 100 mi of dichloromethane and 300 mi of water were added to the resulting mixture to separate layer, and the resulting aqueous mixture was extracted with 300 mi of dichloromethane. The organic layer was dried over magnesium sulfate, concentrated under a reduced pressure, and crystallized at 5 C in 305 mi of isopropanol and 122 mi of water to obtain the white title compound (85.6 g). Then, the filtrate was additionally concentrated under a reduced pressure, and crystallized at 5 C in 30 mi of isopropanol to obtain 12.3 g of the title compound (total: 97.9 g, total yield:%). 1H-NMR (300MHz, CDCl3) delta (ppm): 8.61 (IH), 7.47 (4H), 5.34 (IH), 2.04 (3H)

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. 137234-74-3, 4-Chloro-6-ethyl-5-fluoropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HANMI PHARM. CO., LTD.; WO2009/20323; (2009); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

7226-23-5 , The common heterocyclic compound, 7226-23-5, name is 1,3-Dimethyltetrahydropyrimidin-2(1H)-one, molecular formula is C6H12N2O, 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 diisopropylamine (344 muL, 2.45 mmol) in dry tetrahydrofuran (2.9 mL) was cooled to -78 C. under nitrogen and then treated with a 2.5M solution of n-butyllithium in hexanes (981 muL, 2.45 mmol). The reaction mixture was stirred at -78 C. for 15 min and then treated dropwise with a solution of (4-morpholin-4-yl-phenyl)-acetic acid methyl ester (549.9 mg, 2.34 mmol) in dry tetrahydrofuran (2 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1 mL). The resulting reaction mixture was allowed to stir at -78 C. for 30 min, at which time, a solution of iodomethylcyclopentane (540.0 mg, 2.57 mmol) in a small amount of dry tetrahydrofuran was added dropwise. The reaction mixture was then allowed to warn to 25 C. where it was stirred for 67 h. The reaction mixture was quenched with water and then concentrated in vacuo to remove tetrahydrofuran. The aqueous residue was diluted with ethyl acetate (200 mL). The organic phase was washed with a saturated aqueous sodium chloride solution (1*100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-morpholin-4-yl-phenyl)-propionic acid methyl ester (381.4 mg, 51%) as a white solid: mp 68-70 C.; EI-HRMS m/e calcd for C19H27NO3 (M+) 317.1991, found 317.2001.

According to the analysis of related databases, 7226-23-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Corbett, Wendy L.; Haynes, Nancy-Ellen; Sarabu, Ramakanth; US2002/2190; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia