Pyrimidines

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.22715-27-1, name is 2,5-Diaminepyrimidine, molecular formula is C4H6N4, molecular weight is 110.12, as common compound, the synthetic route is as follows.SDS of cas: 22715-27-1

EXAMPLE 73. Synthesis of N-(2-Amino-Pyrimidin-5-vn-2-ChIoro-S-(3- Trifluoromethvl-BenzovlaimnoVBenzamide (Compound XXXV)XXXV[0254] A solution of intermediate 1 (Example 2) (380 mg, 1.11 mmol) in DCM was charged with CDMT (233 mg, 1.33 mmol), and NMM (0.3 mL, 2.73 mmol). After 1 hr of stirring, 2,5-diaminopyrimidine (121 mg, 1.10 mmol) was added and the solution was allowed to stir for 48 h. The mixture was concentrated and purified by HPLC to afford the title compound as a white solid (350 mg, 73%).[0255] 1H NMR (500 MHz, DMSOd6): delta 7.59 (d, J= 8.8 Hz, IH), 7.81 (t, J= 7.9 Hz, IH), 7.93 (dd, J= 8.8 Hz, J= 2.5 Hz, IH), 8.00 (d, J= 7.8 Hz, IH), 8.02 (d, J= 2.7 Hz, IH), 8.28 (d, J= 8.0 Hz, IH), 8.32 (s, IH), 8.54 (s, 2H), 10.45 (s, IH), 10.71 (s, IH). MS (ES+): m/z 436.0 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22715-27-1, 2,5-Diaminepyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; TARGEGEN, INC.; WO2008/8234; (2008); 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 22536-61-4, name is 2-Chloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Chloro-5-methylpyrimidine

Preparation example 1: Preparation of 5-(bromomethyl)-2-chloropyrimidine 2-chloro-5-methylpyrimidine (12.86 g, 0.1 mol) was dissolved in carbon tetrachloride (300 mL), and N-bromobutanimide (25.72 g, 0.14 mol) and benzoyl peroxide (1.29 g, 5 mmol) were added under stirring. The resultant mixture was heated to reflux by oil bath, and was cooled to room temperature after reacting for 8 h. The mixture was filtrated under suction. The filtrate was concentrated and then subjected to silica gel column chromatography (petroleum ether: acetic ether=1:1) to get the title compound (8.7 g, yield: 42percent).

With the rapid development of chemical substances, we look forward to future research findings about 22536-61-4.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; CHEN, Bo; (105 pag.)EP3091008; (2016); A1;,
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Electric Literature of 4595-59-9, 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 4595-59-9 as follows.

General procedure: In the reaction tube with a magnetic bar was added the solution of aryl bromides (0.5 mmol) and phenylboronic acid (91 mg, 0.75 mmol), NaOH (24 mg, 0.6 mmol), complex 1 (0.0001-0.02 mol%, dissolved in DMA) and ethanol (3 mL). After stirred for the required time in the preset conditions, the reaction mixture was cooled to room temperature, and then quenched by 1 mL brine and 3 mL water, and extracted with ethyl acetate (3×5 mL). The combined organic layer was dried over anhydrous MgSO4 and the filtrate was concentrated to dryness under reduced pressure. The crude products were purified by column chromatography (petroleum ether, ethyl acetate) on silica gel.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-59-9, its application will become more common.

Reference:
Article; Wu, Qinxu; Wu, Leilei; Zhang, Lei; Fu, Haiyan; Zheng, Xueli; Chen, Hua; Li, Ruixiang; Tetrahedron; vol. 70; 21; (2014); p. 3471 – 3477;,
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Synthetic Route of 287714-35-6, 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. 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate, molecular formula is C6H5ClN2O2, 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.

To a suspension of (5,6,7, 8-tetrahydroimidazo[1,2-a]pyrazin-2-yl)-methanol hydrochloride (V, 0.35 g, 1.85 mmol) was added potassium carbonate (0.51 g, 3.71 mmol) at 0 C and stirred at that temperature for 5 min. Then, 2-chloro-pyrimidine-5-carboxylic acid methyl ester (0.38 g, 2.22 mmol) was added and the resulting mixture was stirred at room temperature for 15 h. The reaction mixture was quenched with ice and the solvent was evaporated to get the residue. Water was added and precipitate formed was filtered,ashed with water and n-hexane to afford the pure product as an off-white solid (VI, 0.36 g, 68%). LC-MS m/z calcd for Ci3Hi5N503, 289.1 ; found 290.1 [M+H]+.

According to the analysis of related databases, 287714-35-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JUBILANT BIOSYS LIMITED; RAJAGOPAL, Sridharan; HALLUR, Mahanandeesha S.; DEWANG, Purushottam; MURUGAN, Kannan; KUMAR C.H., Durga Prasanna; IYER, Pravin; MULAKALA, Chandrika; SIVANANDHAN, Dhanalakshmi; NAIR, Sreekala; ZAINUDDIN, Mohd.; TANTRY, Subramanyam Janardhan; GAJENDRAN, Chandru; RAJAGOPAL, Sriram; (334 pag.)WO2017/195216; (2017); A1;,
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Application of 28485-17-8, 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. 28485-17-8, name is 5-Carbethoxyuracil, molecular formula is C7H8N2O4, 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 2. A mixture of ethyl 2,4-dioxo-l,2,3,4-tetrahydropyrimidine-5-carboxylate obtained in step 1 (8.5 g, 46.2 mmol, 1.0 eq), N,N-dimethylbenzenamine (1.12 g, 9.24 mmol, 0.2 eq), POCl3 (21.25 g, 138.6 mmol, 3.0 eq) in benzene (300 mL) was stirred at 9O 0C under a nitrogen atmosphere for 8 h. The reaction mixture was allowed to cool to room temperature and throw into ice (300 g). The mixture was extracted by EtOAc (2×300 mL). The combined organic phases were washed (brine), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel chromatography (PE/EtOAc=500:l to 15:1 as eluent) to afford ethyl 2,4- dichloropyrimidine-5-carboxylate (3.83 g, 37%) as white solid. LC-MS (m/z) =220.9 [M+H]+.

According to the analysis of related databases, 28485-17-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WANG, Tiansheng; HANZELKA, Brian; MUH, Ute; BEMIS, Guy; ZUCCOLA, Harmon, J.; WO2011/19405; (2011); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 26032-72-4, 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 26032-72-4, name is 2,4-Dichloro-6-phenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To the reaction flask were added 2,4-dichloro-6-phenylpyrimidine (0.30 g, 1.30 mmol), potassium carbonate (0.37 g, 2.70 mmol), (R)-methyl 3-amino-4,4-dimethylpentanoate (0.46 g,1.70 mmol) and DMF (10 mL).The mixture was stirred at 80 C for 24 h. Water (40 mL) was added, and the resulting mixture was extracted with EtOAc (30 mL x 3). The combined organic phases were washed with saturated brine (60 mL), dried over anhydrous Na2SO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (v/v) = 15/1) to give the tilte compound as a white solid (120 mg, 26 %).MS (ESI, pos. ion) m/z: 348.1[M+H].

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 26032-72-4, 2,4-Dichloro-6-phenylpyrimidine.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 38696-20-7, 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.38696-20-7, name is 5-Bromo-2-phenylpyrimidine, molecular formula is C10H7BrN2, molecular weight is 235.08, as common compound, the synthetic route is as follows.

Oxazole (124 mg, 1.8 mmol) was dissolved in stirring tetrahydrofuran (20 mL) under nitrogen at -78° C. and treated with n-butyllithium (2.0 M in cyclohexane, 1.1 mL, 2.2 mmol) maintaining internal temperature below -60° C. After stirring ten minutes, ZnCl2 (0.48 g, 3.5 mmol) was added portionwise. The cooling bath was removed and the solution was allowed to reach room temperature. Tetrakis(triphenylphosphine)palladium(0) (30 mg, 5 mole percent) and 5-bromo-2-phenylpyrimidine (309 mg, 1.30 mmol) were added and the mixture heated at 60° C. for four hours. Solvent was removed under reduced pressure and the mixture partitioned between saturated aqueous ammonium chloride and ethyl acetate. The organic phase was retained and additional ethyl acetate extractions of the aqueous phase performed. The combined extracts were dried with anhydrous sodium sulfate, the solution filtered, and solvent removed under reduced pressure. Purification by silica gel flash chromatography (9:1 to 7:3 v/v hexane-ethyl acetate) through a 12-g Silicycle.(R). flash silica cartridge afforded the title compound as an off-white solid (17 mg, 6percent yield); Rf 0.66 with 3:1 v/v hexane-ethyl acetate; melting point 175-177° C.; 1H-NMR (300 MHz; DMSO-d6) delta 9.42 (s, 2H), 8.48 (dd, 2H), 8.41 (s, 1H), 7.56-7.62 (m, 3H), 7.54 (s, 1H); MS (ESI+) m/z 224 (M+1), (ESI-) m/z 222 (M-1); H-PGDS FPBA IC50: 7.8 muM.

The chemical industry reduces the impact on the environment during synthesis 38696-20-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CAYMAN CHEMICAL COMPANY; US2010/75990; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 6972-27-6, 6-Chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

Method C: The stirred solution of solution of 6-chloro-l ,3-dimethylpyrimidine- 2,4(lH,3H)-dione (1 Kg) in ethanol (12 L) was added portion wise sodium hydrosulphide hydrate (1 kg) over a period of 1 h at 0 to 5C. After addition, the reaction mixture was stirred at 25 to 30C for 2 h. The reaction mixture was filtered and washed with ethanol (2 L). The filtrate was collected and concentrated under vacuum to obtain residue which was then dissolved in water (8 L). The aqueous solution was washed with dichloromethane (3 L) followed by petroleum ether (2 L). The aqueous layer was separated and was acidified using hydrochloric acid solution [4 L, cone, hydrochloric acid and water (1 : 1)]. The precipitated solid was filtered and washed with water followed by ethanol and dried to obtain the 0.8 Kg of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6972-27-6, 6-Chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; KADAM, Suresh Mahadev; THOMAS, Abraham; SINHA, Sukumar; KUMAR, Sukeerthi; KANSAGRA, Bipin Parsottam; GAVHANE, Sachin; KHANDAGALE, Sandeep Bandu; PAWASE, Shailesh; PATIL, Jayant Prakashrao; BHADANE, Shailendra; MISHRA, Bhavna; DWIVEDI, Rajesh; WO2013/183035; (2013); A2;,
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Pyrimidine – Wikipedia

Related Products of 926663-00-5, 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.926663-00-5, name is Ethyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C9H9N3O3, molecular weight is 207.19, as common compound, the synthetic route is as follows.

The 5-hydroxy pyrazole [1,5-a] pyrimidine-3-carboxylic acid ethyl ester (20.8g), tetrahydrofuran (223 ml) and ethanol (111 ml) is added in the mixture 2M of aqueous sodium hydroxide solution (201 ml). In the reaction mixture is 50 C stirring overnight, and the evaporation of the organic solvent under reduced pressure. Adding the aid hemostasis 2M hydrochloric acid (201 ml), will precipitate and collect the solid by filtration, but also to water/ethanol cleaning and generates a title compound (17.7g).

Statistics shows that 926663-00-5 is playing an increasingly important role. we look forward to future research findings about Ethyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; TAKED A PHARMACEUTICAL COMPANY LIMITED; KAWASAKI, MASANORI; MIKAMI, SATOSHI; NAKAMURA, SHINJI; NEGORO, NOBUYUKI; IKEDA, SHUHEI; ASHIZAWA, TOMOKO; MARUI, SHOGO; TANIGUCHI, TAKAHIKO; (135 pag.)TW2016/520; (2016); A;,
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Pyrimidine – Wikipedia

Synthetic Route of 14080-23-0, 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. 14080-23-0, name is 2-Cyanopyrimidine, molecular formula is C5H3N3, 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-2:Preparation of 2-amidinopyrimidinium hydrochloride (II)2-Cyanopyrimidine (XIII) (5Og, 475.73 mmol) was added to the solution of sodium ethoxide (3.24g, 47.64 mmol) in methanol (500 ml) at -3 to O0C and was stirred for 8 hrs. The reaction mass was allowed to a temperature of 25-3O0C and treated with ammonium chloride (26.72g, 499.43 mmol) to yield 2-amidinopyrimidinium hydrochloride (II).

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 14080-23-0, 2-Cyanopyrimidine.

Reference:
Patent; AUROBINDO PHARMA LIMITED; BRAJESH, Kumar, Sinha; KONDURU, Rajasekhara, Raju; BUDIDET, Shankar, Reddy; VADDI, Pandu, RangaRao; AMINUL, Islam; MEENAKSHISUNDERAM, Sivakumaran; WO2011/24056; (2011); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia