Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 659729-09-6, 4-Chloro-6-(4-(trifluoromethyl)phenyl)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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

4-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine (2.55 g, 9.86 mmol) was dissolved in CH3CN (50 ml) and cooled to 0C. Tetrabutylammonium cyanide (4.55 g, 16.9 mmol) and DABCO (3.32 g, 29.6 mmol) were added and the reaction mixture was stirred at 0C for 2 hours. The reaction mixture was then absorbed onto a small amount of silica gel and purified by flash column (0-20% EtOAc over 35 min) to give 6-(4-(trifluoromethyl)phenyl)pyrimidine-4-carbonitrile as a white solid (2.26 g; 92%).

The synthetic route of 659729-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine E.; CHEN, Huifen; CHEN, Shaoqing; CHEN, Zhi; ERICKSON, Shawn David; ESTRADA, Anthony; KIM, Kyungjin; LI, Hongju; LOVEY, Allen John; LYSSIKATOS, Joseph P.; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter Michael; YI, Lin; WO2014/49047; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 514854-13-8 ,Some common heterocyclic compound, 514854-13-8, molecular formula is C6H9IN4, 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: The alkyne (1.2 eq), iododiaminoethyl pyrimidine (1.0 eq) was dissolved in anhydrous DMF (0.15M) and sonicated under argon. Pd(PPh3)2Cl2 (0.1 eq), CuI (0.21 eq), Et3N (24 eq) were added and again sonicated under argon for 15 minutes. The reaction mixture was heated at 60 C for 12h under argon. The reaction mixture was then concentrated in vacuo before preabsorbing onto a mixture of amine and 25% cysteine preabsorbed silica gel (1:1 /wt) and filterted through a plug of silica gel with 5% MeOH/ CH2Cl2. The collected reaction mixture was concentrated in vacuo, and further purified by preparative HPLC to furnish the final product

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. 514854-13-8, 6-Ethyl-5-iodopyrimidine-2,4-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lombardo; Dayanandan; Keshipeddy; Zhou; Si; Reeve; Alverson; Barney; Walker; Hoody; Priestley; Obach; Wright; Drug Metabolism and Disposition; vol. 47; 9; (2019); p. 995 – 1003;,
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. 123148-78-7, name is 4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 123148-78-7

DMF (66mL) was added to a mixture of compound 12 1 (2.00g, 7.15mmol) and 59 sodium hydride (243mg, 10.1mmol) under nitrogen atmosphere. The reaction mixture was cooled to 0C and stirred for 30min. 60 2-(Trimethylsilyl)-ethoxymethyl chloride (1.70mL, 9.58mmol) was added dropwise over 45min and stirred at 22C for 1.5h. 61 Water (150mL) and 62 EtOAc (150mL) was added to the reaction mixture, the phases were separated, and the water phase was extracted with more EtOAc (2¡Á150mL). The combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. The product was purified by silica-gel column chromatography (n-pentane/EtOAc, 1/1, Rf=0.78) to give 2.74g (10.0mmol, 86%) of a pale yellow 63 powder; mp. 98-104C; 1H NMR (400MHz, DMSO-d6): 8.69 (s, 1H), 8.13 (s, 1H), 5.60 (s, 2H), 3.51 (t, J=8.1, 2H), 0.82 (t, J=8.1, 2H),-0.10 (s, 9H). The spectroscopic data corresponded with that reported previously [40].

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, 123148-78-7, 4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Article; Reiers¡ãlmoen, Ann Christin; Han, Jin; Sundby, Eirik; Hoff, Bard Helge; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 562 – 578;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3177-20-6, Methyl 2,4-dichloropyrimidine-5-carboxylate, 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, COA of Formula: C6H4Cl2N2O2, blongs to pyrimidines compound. COA of Formula: C6H4Cl2N2O2

To a solution of 2,4-dichloropyrimidine-5-carbonyl chloride (500 mg, 2.38 mmol) in dichloromethane (30 mL) was added methanol (87.6 mg, 2.73 mmol) and diisopropylethylamine (369 mg, 2.86 mmol) at 0 ¡ãC. The resulting mixture was stirred for at 0 ¡ãC 1 h. Then the solvent was removed. The residue (412mg, 2.0 mmol) was dissolved in IPA (20 mL) followed by the addition of Z-Ormthine (465 mg, 2.0 mmol) and N,N- diisopropylethylamine (388 mg, 3.0 mmol). The resulting mixture was stirred at 0 ¡ãC for 90 min, then dichloromethane (5.0 mL) was added. The resulting mixture was stirred at 0 ¡ãC for 1.0 h and at room temperature overnight. Solvent was removed and the residue (MS m/z 403.30 [M+H]+) was dissolved in DMF (5.0 mL) and was added dropwise into a solution of 1,4-diaminobutane (1.68g, 19.1 mmol) in DMF (1.0 mL) at room temperature. The resulting mixture was heated to 45 ¡ãC for l . The solvent was removed and the residue was dissolved in ethyl acetate (35 mL) and washed with water (3x). The organic layer was dried ( a2S04), filtered and concentrated. The residue was purified on HPLC to provide (S)-5-((2-((4- aminobutyl)amino)-5-(methoxycarbonyl)pyrimidin-4-yl)amino)-2-((tert-butoxycarbonyl) amino)pentanoic acid as a semisolid (MS m/z 455.30 [M+H]+). The semisolid (595 mg, 1.31 mmol) was dissolved in DMF (150 mL), then TBTU (546.4 mg, 1.70 mmol) and DIEA (508 mg, 3.93 mmol) were added sequentially. The resulting mixture was stirred at room temperature overnight. The solvent was removed. The residue was dissolved in ethyl acetate and washed with water (3x). The organic layer was dried (Na2S04), filtered and concentrated. The residue was purified on HPLC to provide the totle compound (UNC2343A). 1H NM (400 MHz, CD3OD) S 8.42 (s, 1H), 4.08-3.99 (m, 1H), 3.90-3.84 (m, 3H), 3.59-3.47 (m, 2H), 3.46-3.31 (m, 2H), 3.28-3.21 (m, 1H), 3.09-2.95 (m, 1H), 1.90-1.52 (m, 8H), 1.51- 1.32 (m, 9H); MS m/z 437.30 [M+H]+.

The synthetic route of 3177-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WANG, Xiaodong; ZHANG, Weihe; FRYE, Stephen; WO2015/157127; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 63558-65-6, Adding some certain compound to certain chemical reactions, such as: 63558-65-6, name is 4-Chloro-5-iodopyrimidine,molecular formula is C4H2ClIN2, 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 63558-65-6.

Preparation 57A: 5-Iodo-4-(2H-l,2, -triazol-2-yl)pyrimidine[00244] To a solution of lH-l,2,3-triazole (63.2 mg, 0.915 mmol) in THF (Volume: 241 1 ??), was added portion wise at 0 C, NaH (39.9 mg, 0.998 mmol). The reaction mixture was stirred at that temperature for 30 min, then 4-chloro-5-iodopyrimidine (200 mg, 0.832 mmol) was added. The reaction mixture was allowed to warm to room temperature. To this solution was added saturated aqueous NH4C1 and the mixture was allowed to stir for 5 min at which time it was diluted with ethyl acetate and extracted 2X. The combined organics were washed with brine IX. The organics were dried overNa2S04, filtered and concentrated in vacuo to afford the title compound (90 mg, 40%).

According to the analysis of related databases, 63558-65-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; VELAPARTHI, Upender; LIU, Peiying; WO2013/49263; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 955368-90-8 , The common heterocyclic compound, 955368-90-8, name is 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, molecular formula is C9H10N4OS, 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.

Into a 25 mL microwave vial was added 2-allyl-6-(methylthio)-1H-pyrazolo[3,4- d]pyrimidin-3(2H)-one (275 mg, 1.235 mmol) (obtained according to EP2213673B1, Production Example 1, p37), [(5-bromopyridin-3-yl)imino]dimethyl-A6-sulfanon (400 mg, 1.61 mmol), potassium carbonate (239 mg, 1.73 mmol) and dioxane (5 mL). The resultant suspension was degassed (bubbling of N2) and copper (I) iodide (235 mg, 1.235 mmol) was added followed by N1,N2-dimethylethane-1,2-diamine (0.133 mL,1.24 mmol). The vial was capped and the reaction mixture was stirred at 95 00 overnight. After cooling to RT the reaction mixture was transferred to a separation funnel, NH4OH (aq, 20 mL) was added and the resulting mixture was extracted with EtOAc (3 x 30 mL). The organic phases were combined, dried and evaporated under vacuum. The residue was purified using flash chromatography (0-15% MeOH in EtOAc). The product containing fractions were concentrated to give the title compound (60 mg, 12.44 % yield) as an yellowish oil that solidified upon storage. LCMS (Method C): RT = 0.99 mi mlz = 391 [M+H].1H NMR (300 MHz, ODd3) O 9.21 (5, 1H), 8.64 (5, 1H), 8.57 (5, 1H), 8.12 (5, 1H),5.70-5.41 (m, 1H), 5.17 (t, J = 5.1 Hz, 1H), 4.96 (d, J = 17.0 Hz, 2H), 4.53 (d, J = 6.0 Hz, 2H), 3.31 (5, 6H), 2.53 (5, 3H)

The synthetic route of 955368-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BURKAMP, Frank; ROUNTREE, James Samuel Shane; TREDER, Adam Piotr; (155 pag.)WO2018/11569; (2018); A1;,
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.50593-92-5, name is 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid, molecular formula is C6H5BrN2O2S, molecular weight is 249.09, as common compound, the synthetic route is as follows.Safety of 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid

A catalytic amount of N,N-dimethylformamide (2 drops) was added to a stirred suspension of 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (2.07 g, 8.33 mmol) and a 2 M solution of oxalyl chloride (21 mL, 0.042 mol) in dichloromethane under nitrogen at r.t. Vigorous effervescence was observed. After 30 min everything had dissolved and the solvent was then evaporated in vacuo. The residue was dissolved in dichloromethane (20 mL) and placed under nitrogen. Triethylamine (2.32 mL, 16.66 mmol) was added to this stirred solution at r.t. followed by 4-aminopyridin-3-yl diethylcarbamodithioate (2.01 g, 8.33 mmol). Everything quickly dissolved with a noticeable exotherm. After 3 h at r.t. tic showed a new major product. The reaction was diluted with dichloromethane (20 mL) and washed with a saturated aqueous solution of sodium hydrogen carbonate (40 mL). The organic layer was separated, dried over sodium sulfate, filtered and the solvent evaporated in vacuo. The residue was purified by flash chromatography (ethyl acetate / hexane 15:85 to 60:40) to yield 4-(5-bromo-2- (methylthio)pyrimidine-6-carboxamido)pyridin-3-yl diethylcarbamodithioate (1.99 g, 51%) as a pale yellow amorphous solid. 1H NMR : delta (CDCl3, 400 MHz) 1.30 (t, J = 7 Hz, 3 H), 1.51 (t, J= 7 Hz, 3 H), 2.60 (s, 3 H), 3.93 – 4.08 (m, 4 H), 8.57 – 8.62 (m, 2 H), 8.69 (d, J = 6 Hz, 1 H), 8.85 (s, 1 H), 10.67 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,50593-92-5, 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN, INC.; WO2006/66172; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 183438-24-6, 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. 183438-24-6, name is 5-Bromo-2-iodopyrimidine, molecular formula is C4H2BrIN2, 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.

5-Bromo-2-iodopyrimidine (2 g, 7.02 mmol) was dissolved in dry toluene (30 mL) and cooled to -78 C under nitrogen. A 2.5M solution of n-BuLi in hexane (2.95 mL) was added drop wise and the reaction stirred for 15 minutes prior to the drop wise addition of tetrahydro-4H-pyran-4-one (0.77 g, 7.72 mmol). The reaction was stirred at -78 C for 30 min and then was allowed to warm to r.t.. The reaction mixture was diluted with water – -(50 mL) and extracted with EtOAc (2 x 50mL). The combined organic extracts were dried over magnesium sulfate and the solvent removed under reduced pressure to afford 1.9 lg of crude product as an orange oil. The crude orange oil was purified by flash column chromatography (Si02, 10-100% EtOAc in heptane) to afford 762 mg (42 %) of the title compound as a yellow oil.1H NMR (500 MHz, CDC13) delta ppm 8.79 (s, 2H), 4.24 (s, 1H), 3.99 – 3.89 (m, 4H), 2.37 (td, J 12.3, 11.6, 6.3 Hz, 2H), 1.54 (dd, J 13.6, 2.0 Hz, 2H).

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 183438-24-6, 5-Bromo-2-iodopyrimidine.

Reference:
Patent; UCB BIOPHARMA SPRL; ALEXANDER, Rikki, Peter; BRACE, Gareth, Neil; BROWN, Julien, Alistair; CALMIANO, Mark, Daniel; CHOVATIA, Praful, Tulshi; DELIGNY, Michael; GALLIMORE, Ellen, Olivia; HEER, Jag, Paul; JACKSON, Victoria, Elizabeth; KROEPLIEN, Boris; MAC COSS, Malcolm; QUINCEY, Joanna, Rachel; SABNIS, Yogesh, Anil; SWINNEN, Dominique, Louis, Leon; ZHU, Zhaoning; WO2015/86526; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 18740-39-1, 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. 18740-39-1, name is 2,4-Dichlorothieno[2,3-d]pyrimidine, molecular formula is C6H2Cl2N2S, 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.

General procedure: To a solution of 2,4-dichloro-5-fluoroquinazoline (22a) (100.00mg, 460.77 mumol, 1.00 eq) in THF (3.00mL) was added methyl (2S,3S)-3-aminobicyclo[2.2.2]octane-2-carboxylate (84.44mg, 460.77 mumol, 1.00 eq) and DIPEA (238.20mg, 1.84mmol, 4.00 eq) at room temperature overnight. H2O (20mL) was added to the mixture and extracted with EtOAc (10mL¡Á3). The combined organic layers were dried over Na2SO4 and concentrated in vacuum. The residue was purified by column chromatography on silica gel with PE:EtOAc (10:1 to 5:1) to give compound 23a (130.00mg, 357.33 mumol, 77.55% yield) as a yellow solid.

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 18740-39-1, 2,4-Dichlorothieno[2,3-d]pyrimidine.

Reference:
Article; Xiong, Jian; Wang, Jingjing; Hu, Guoping; Zhao, Weili; Li, Jianqi; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 249 – 265;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 74901-69-2, 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. 74901-69-2, name is 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine, molecular formula is C6H4Cl2N2S, 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.

8.3 [1-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)-cyclopropyl]-methanol (III-4) 1.4 g (II) are placed in 10 ml dioxane, then first 3.6 ml diisopropylethylamine are added followed by 1 g 1-aminocyclopropanemethanol (cf. 8.2). The reaction mixture is heated to 160 C. until there is no further reaction, then cooled and evaporated down. The residue is treated with cyclohexane/ethyl acetate (8:2) in the ultrasound bath and the solid is suction filtered and dried. 1.24 g (III-4) are obtained in the form of a solid. Analytical HPLC-MS (method A): RT=1.01 min.

According to the analysis of related databases, 74901-69-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/28932; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia