Category: pyrimidines

Reference of 53135-24-3 ,Some common heterocyclic compound, 53135-24-3, molecular formula is C8H10N2O3, 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.

General procedure: Compound 17 c (2.90 g, 21 mmol) and diethyl (ethoxymethylidene)propanedioate (4.25 mL, 21 mmol) were dissolved in EtOH (30 mL). A solution of sodium ethoxide (20% in EtOH; 14.3 g, 42 mmol) was added to the solution dropwise at 0 C. After stirring at 80 C for 15 h, the reaction mixture was concentrated in vacuo. The residue was acidified with 1M HCl to pH 3. The precipitate was collected by filtration and washed with small amount of water. The product obtained (2.90 g, 13 mmol) was dissolved in POCl3 (9.6 g). After stirring at 100 C for 2 h, the reaction mixture was concentrated in vacuo. The residue was cooled to 0 C, neutralized with a saturated aqueous NaHCO3 solution to pH 7, and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and concentrated in vacuo. A solution of the product obtained, furfurylamine (1.20 mL, 12.9 mmol), and diisopropylethylamine (2.26 mL, 12.9 mmol) in 2-propanol (10 mL) was stirred under reflux for 15 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with a saturated aqueous NaHCO3 solution and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc=9:1 to 5:1). The product obtained was dissolved in 2M NaOH (15mL, 30mmol), EtOH (15mL), and THF (5mL). After stirring at room temperature for 15h, the mixture was acidified with 1M HCl to pH 3.0. The precipitate was collected by filtration and washed with water to give 18c as a colorless powder (3.30g, 57%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53135-24-3, its application will become more common.

Reference:
Article; Imaeda, Yasuhiro; Tawada, Michiko; Suzuki, Shinkichi; Tomimoto, Masaki; Kondo, Mitsuyo; Tarui, Naoki; Sanada, Tsukasa; Kanagawa, Ray; Snell, Gyorgy; Behnke, Craig A.; Kubo, Keiji; Kuroita, Takanobu; Bioorganic and Medicinal Chemistry; vol. 24; 22; (2016); p. 5771 – 5780;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 17180-94-8, Adding some certain compound to certain chemical reactions, such as: 17180-94-8, name is 5-Chloropyrimidine,molecular formula is C4H3ClN2, 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 17180-94-8.

A 100 mL round-bottom flask was charged with 5-chloropyrimidine (5 mmol), phenylboronic acid (1.22 g, 10 mmol), PPh3 (265 mg, 1 mmol) and Pd(OAc)2 (224 mg, 1 mmol) in dioxide (50 mL) under nitrogen at room temperature. After stirring for 30 minutes, Na2C03 (159 mg, 7.5 mmol) and H20 (10 mL) were added and the resulting mixture was heated at reflux for 3 h. After cooling to rt, the reaction mixture was poured into water and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine (3 x 50 mL) and dried over anhydrous Na2S04. After filtration and concentration, the crude product was purified by column chromatography to give the title compound.

According to the analysis of related databases, 17180-94-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNOVION PHARMACEUTICALS INC.; CAMPBELL, John, Emmerson; CAMPBELL, Una; HANANIA, Taleen, G.; SHAO, Liming; WO2013/119895; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 14631-08-4 , The common heterocyclic compound, 14631-08-4, name is 2-Chloropyrimidine-4,5-diamine, molecular formula is C4H5ClN4, 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.

Compound 21-3 (4 g, 27.6 mmol) and compound 21-3-1 (5.2 g, 31.2 mmol) were dissolved in HCl/i-PrOH (2 mL/40 mL), and the mixture was heated to 100 C. and stirred for 14 h, followed by adjusted to pH 9 with Na2CO3 (aq.) and extracted with DCM (50 mL×4). The organic phase was dried over anhydrous Na2SO4, filtered and concentrated to give a crude product which was purified by column chromatography to afford compound 21-4 (1.1 g, Yield 14.7%) as black solid.

The synthetic route of 14631-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.; Humanwell Healthcare (Group) Co., Ltd.; Wang, Xuehai; Wu, Chengde; Xu, Yong; Shen, Chunli; Li, Li’e; Hu, Guoping; Yue, Yang; Li, Jian; Guo, Diliang; Shi, Nengyang; Huang, Lu; Chen, Shuhui; Tu, Ronghua; Yang, Zhongwen; Zhang, Xuwen; Xiao, Qiang; Tian, Hua; Yu, Yanping; Chen, Hailiang; Sun, Wenjie; He, Zhenyu; Shen, Jie; Yang, Jing; Tang, Jing; Zhou, Wen; Yu, Jing; Zhang, Yi; Liu, Quan; (251 pag.)US2017/313683; (2017); A1;,
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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. 108-53-2, name is 2-Aminopyrimidin-4(1H)-one, molecular formula is C4H5N3O, 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. HPLC of Formula: C4H5N3O

Step 1-Synthesis of 2-amino-5-nitro-3,4-dihydropyrimidin-4-one Concentrated sulfuric acid (2.4 mL) was added to 2-amino-3,4-dihydropyrimidin-4-one (1 g, 9.0 mmol). The mixture was stirred and cooled in ice bath before dropwise addition of concentrated nitric acid (0.56 mL). The mixture was stirred at RT for 30 min before being heated at 70 C. for 2 hr. The mixture was allowed to cool to RT and was slowly added to water (10 mL), cooled in an ice bath. The resultant precipitate was collected by suction filtration, washed with diethyl ether (5 mL) and then thoroughly dried under high vacuum to give the title compound: 1H NMR (250 MHz, DMSO) delta 7.18 (1H, br. s.), 8.61 (1H, br. s.), 8.81 (1H, s); LC-MS: m/z=+156.9 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 108-53-2.

Reference:
Patent; Genentech, Inc.; US2012/214762; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1439-08-3, 5-Bromo-4-(tert-butyl)pyrimidine, 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, Product Details of 1439-08-3, blongs to pyrimidines compound. Product Details of 1439-08-3

To a stirred solution of commercially available 5-bromo-4-(tert-butyl)-pyrimidine (215 mg, 1 mmol) in THF (1 ml) and toluene (4 ml) was added triisopropyl borate (229 mg, 282 tl, 1.22 mmol) at -78 C followed by a drop-wise addition of n-butyl lithium (1 .6N in hexane) (731 tl, 1.17 mmol) at -78 C. The solution was allowed to stir at -78 C for 45 mm and then allowed to warm to room temperature. The reaction mixture was quenched by addition of 1M hydrochloride solution (2.5 ml) to pH = 1, diluted with water (5 ml) and extracted with diethyl acetate (2 x 40 ml). The combined organic layers were washec with brine (30 ml), dried (Mg504) and evaporated to yield (4-(tert-butyl)-pyrimidin-5-yl)-boronic acid (135 mg) as a light yellow oil, MS (ISP) mz = 181.1 [(M+H)i, which was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1439-08-3, 5-Bromo-4-(tert-butyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HOENER, Marius; WICHMANN, Juergen; (55 pag.)WO2017/72083; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 6960-17-4, 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. 6960-17-4, name is 2,5-Dimethoxypyrimidin-4-amine, molecular formula is C6H9N3O2, 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.

Example 6Preparation of Ethyl [(2,5-dimethoxypyrimidin-4-yl)amino]carbono-thioylcarbamate 2,5-Dimethoxypyrimidin-4-amine (6) (3 g, 0.0193 moles) was dissolved in 18 g of ethyl acetate. Ethyl isothiocyanatidocarbonate (2.77 g, 0.0208 moles) was added in one portion. The solution was heated to 78 C. and held at that temperature for 11 h. An additional 1.4 g of the ethyl isothiocyanatidocarbonate was added and the mixture heated for 2.5 h. The mixture was allowed to cool to 22 C. and filtered. The resulting solid was washed with ethyl acetate (20 mL) and dried to a constant weight in a fume hood to afford the title compound as a yellow solid (4.81 g, 89%): 13C NMR (DMSO-d6, 100 MHz) delta 177.5, 158.4, 153.3, 149.5, 142.3, 139.5, 62.6, 57.6, 55.2, 14.4; HRMS (ESI), calcd for C10H14N4O4S, 286.0736; found, 286.0727.

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 6960-17-4, 2,5-Dimethoxypyrimidin-4-amine.

Reference:
Patent; DOW AGROSCIENCES LLC; US2011/295003; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 890094-38-9, 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. 890094-38-9, name is 2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine. A new synthetic method of this compound is introduced below.

Step 2(3a) (4a)Compound (3a) (90.9 g, 0.420 mol), tetrahydrofuran (840 mL, abs.), Pt/C 5% (9.0 g, 42 mmol) and vanadyl acetylacetonate (4.5 g, 16 mmol) are added in a Parr apparatus and shaken under a hydrogen pressure of 50 psi at 20 C to 40 C for several hours until the reduction of the nitro group is complete (TLC control: silica gel, CH : EE = 1 : 1 ). The catalyst is removed and the solvent is evaporated under reduced pressure. The crude product is dissolved in a mixture of tetrahydrofuran (100 mL) and isopropanol (120 mL) and transferred into a three necked flask. Trimethylchlorosilane (54 ml) is added dropwise and the hydrochlorid precipitates. The suspension is stirred for 16 hours. The precipitate is suction filtered and dried. Yield: 54.8 g (59 % of theory) of compound (4a) as brown crystalline solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,890094-38-9, 2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LINZ, Guenter; BISCHOFF, Daniel; EBNER, Thomas; WO2011/101369; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 20924-05-4, 2-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetic acid, 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, 20924-05-4, blongs to pyrimidines compound. COA of Formula: C7H8N2O4

EXAMPLE 64. 1-(4-METHYL-THIAZOLE-2-SULFONYL)-4-[(THYMIN-1-YL)-ACETYL]-PIPERAZIN-2- one [00377] To 3 mL of DMF, were added 0.30 g (0.8 mmol) OF 4- (4-METHYL-THIAZOLE-2-SULFONYL)- piperazin-2-one trifluoroacetic acid salt, 0.147 g (0.8 mmol) of (thymin-1-yl)-acetic acid and 0.458 g of PYBOP. The reaction mixture was stirred for 4hours at room temperature. Almost of the solvent was removed in vacuo and the residue was dissolved in methylene chloride. The solution was washed with saturated sodium bicarbonate solution, water, 1N HCI, water and brine sequencially. The organic layer was concentrated and column chromatographed on silicagel to give 0.19 g (56%) OF THE title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,20924-05-4, its application will become more common.

Reference:
Patent; PANAGENE INC.; WO2005/9998; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 43088-67-1, 4-Chloro-5-methylthieno[2,3-d]pyrimidine, 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, Formula: C7H5ClN2S, blongs to pyrimidines compound. Formula: C7H5ClN2S

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine (32 mg), 2-phenyl-[1,8]naphthyridin-3-ol (39 mg), and 4-dimethylaminopyridine (64 mg) were suspended in 1,2-dichlorobenzene (1 ml), and the suspension was stirred at 130C for 2.5 hr. The reaction mixture was cooled to room temperature, and an aqueous sodium hydrogencarbonate solution was added to the reaction mixture. The organic layer was extracted with chloroform, and the chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give the title compound (62 mg, yield 99%). 1H-NMR (CDCl3, 400 MHz): delta 2.61 (d, J = 1.2 Hz, 3H), 7.09 (d, J = 1.5 Hz, 1H), 7.31 – 7.35 (m, 3H), 7.54 (dd, J = 4.1, 8.1 Hz, 1H), 7.92 (m, 2H), 8.15 (s, 1H), 8.25 (dd, J = 1.7, 8.1 Hz, 1H), 8.42 (s, 1H), 9.17 (dd, J = 2.0, 4.1 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 371 (M+1)+

The synthetic route of 43088-67-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1724268; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 946161-16-6, 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. 946161-16-6, name is (R)-Methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(isopropyl)amino)butanoate, molecular formula is C12H17ClN4O4, 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.

Step 3 (7R)-2-Chloro-7-ethyl-8-isopropyl-5,7-dihydropteridin-6-one Methyl (2R)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]butanoate 22b (7.30 g, 23 mmol) was dissolved in 100 mL acetic acid followed by the addition of 5g Raney nickel, repeated filled with hydrogen for three times. The reaction mixture was heated to 75 C., stirred for 2 hours and filtered. The filtrate was concentrated under reduced pressure, added with 30 mL of ice water resulting in the formation of precipitate. The precipitate was filtered. the filter cake was dried by heat to obtain the crude title compound (7R)-2-chloro-7-ethyl-8-isopropyl-5,7-dihydropteridin-6-one 22c (12.10 g, yield: 71.7%) as a gray solid, which was used in the next step without further furification.MS m/z (ESI): 255.1 [M+1]

According to the analysis of related databases, 946161-16-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHANGHAI HENGRUI PHARMACEUTICAL CO., LTD.; JIANGSU HENGRUI MEDICINE CO., LTD.; US2012/184543; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia