Month: March 2022

Reference of 69785-94-0, 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 69785-94-0 as follows.

Step 2. 3-{2-cyano-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}-N-(4-hydroxypyrimidin-5-yl)pyrrolidine-1-carbothioamide5-Aminopyrimidin-4-ol (52.4 mg, 0.203 mmol) was dissolved in pyridine (0.55 mL) and phenyl chlorothionocarbonate (33 microL, 0.24 mmol) was added. The mixture was stirred at RT for one h. The reaction was diluted with DCM and washed with water and brine, the organic phase was dried over sodium sulfate and concentrated. The residue was dissolved in chloroform (1.7 mL), and triethylamine (141 microL, 1.01 mmol) and 3-pyrrolidin-3-yl-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (75 mg, 0.17 mmol; from Example 15, Step 3) were added. The mixture was stirred for 30 min at 70 C. The solvents were removed in vacuo and the product was purified by preparative-HPLC/MS (C18 column eluting with a gradient of ACN/H2O containing 0.15% NH4OH) (15 mg, 15%). LCMS (M+H)+: 591.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69785-94-0, its application will become more common.

Reference:
Patent; Rodgers, James D.; Shepard, Stacey; Arvanitis, Argyrios G.; Wang, Haisheng; Storace, Louis; Folmer, Beverly; Shao, Lixin; Zhu, Wenyu; Glenn, Joseph; US2010/298334; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 2908-71-6, Adding some certain compound to certain chemical reactions, such as: 2908-71-6, name is 5-(Bromomethyl)-2-methylpyrimidin-4-amine hydrobromide,molecular formula is C6H9Br2N3, 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 2908-71-6.

On the o ther hand, trisdibenzylieneacetone dipalladium (1.1 mg, 1.2 **mol) and the NMPsolution (200 muL) of triotolyl phosphine (5.8 mg, 19.1 **mol) were prepared for thereaction container of the sign synthesizer unit, and it installed in the room temperature. Thesolution in a reaction container was installed in 10 20 quota which blows a [ C] methyliodide. Then, a [ C] methyl iodide is blown into a reaction container by the gas mass flow of6080 mL/min, The NMP solution (100 muL) of the tin precursor 2 (5.0 mg, 11.9 **mol), CuBr(0.9 mg, 5.9 **mol), and CsF (2.3 mg, 14.9 **mol) was added there, and it heated for 3minutes at 100 degrees C. Then, the DMF solution (100 **L) of 4amino5(bromomethyl)2methylpyrimidine bromate (50 mg, 176.7 **mol) was added, and it heated for 7 minutes at150 degrees C, blowing nitrogen gas by the flow rate of 20 mL/min. After diluting the obtainedreaction solution with the washing liquid (acetonitrile: water =1:1) of 1.2 mL, it filtered usingthe filter. The fraction which presents preparative isolation HPLC with a filtrate (refer to Fig.1),and contains the Csign thiamin 4 isolated preparatively was concentrated in vacuum in theevaporator. Preparative isolation HPLC was again presented with the filtrate obtained bycarrying out filter filtration of the concentrate (refer to Fig.2). The fraction containing the 11C-thiamin 4 isolated preparatively was put into the membrane filter at the sterile vialthrough the concentrate obtained by concentrating in vacuum in an evaporator.

According to the analysis of related databases, 2908-71-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RIKEN; Watanabe, Yasuyoshi; Suzuki, Masaaki; Doi, Hisashi; Nozaki, Satoshi; Kanazawa, Shomasaru; Mawatari, Aya; (25 pag.)JP6037330; (2016); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 192869-80-0, 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.192869-80-0, name is 7-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine, molecular formula is C14H14ClN3, molecular weight is 259.73, as common compound, the synthetic route is as follows.

Step 4: 4-(dimethoxymethyl)-2-methoxypyrimidine, 60 is prepared as follows: 4-(dimethoxymethyl)-2-(propylthio)pyrimidine, 59, is dissolved in methanol (40 mL) and sodium methoxide (1.57 g) is added. The mixture is heated to 60 C. for 1 h, then the solvent removed in vacuo. The residue is partitioned between ethyl acetate and water, extracting the aqueous layer with further ethyl acetate. The combined organics are dried (magnesium sulfate), filtered and concentrated to give the title compound (4.53 g) as an oil. The compound obtained in this step shows the following mass spectral data: LC/MS: C8H12N2O3 requires 184.1; observed M/Z 185.2 [M+H]+. RT 2.57 min.

Statistics shows that 192869-80-0 is playing an increasingly important role. we look forward to future research findings about 7-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine.

Reference:
Patent; Griffin, John; Lanza, Guido; Yu, Jessen; US2005/261354; (2005); 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. 60025-06-1, name is 1-(4,6-Dichloropyrimidin-5-yl)ethanone. A new synthetic method of this compound is introduced below., Safety of 1-(4,6-Dichloropyrimidin-5-yl)ethanone

EXAMPLE 53 -A; 4-(4-(4-(4-fluoro-3-(trifluoromethyl)phenyl)-l -methyl- lH-imidazol-2-yl)piperidin-l-yl)-3-methyl-lH-pyrazolo[3,4-t/1pyrimidine; In a microwave vial charge 4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-l-methyl- lH-imidazol-2-yl]-piperidine dihydrochloride salt (0.5g, l.Oeq), l-(4,6-dichloro- pyrimidin-5-yl)-ethanone (0.22g, l.Oeq), TEA (1.2 mL, 8.0eq) and isopropyl alcohol (5 mL). Stirr the reaction mass at 800C for 45 min in microwave. Monitor the reaction by TLC (10% MeOH in DCM). Cool the reaction mass to 00C and add hydrazine hydrate (0.07 mL, 1.2eq). Slowly bring the reaction mass to RT. Stirr the reaction mass at 800C for 45min in microwave. Monitor the reaction by TLC (10% MeOH in DCM). Concentrate the reaction mass under vacuum. Charge ethyl acetate and then wash with water and saturated aq. sodium chloride. Dry the organic layer over anhydrous Na2SO4 and concentrate it under reduced pressure. Purify the compound by column chromatography (Silica gel 60-120 mesh, DCM – Methanol). Crystallize the product in diethyl ether and filter it to give 4-(4-(4-(4-fluoro-3-(trifluoromethyl)phenyl)-l-methyl- lH-imidazol-2-yl)piperidin-l-yl)-3-methyl-lH-pyrazolo[3,4-betaT|pyrimidine (0.254g,50.29%). MS (M+eta): m/z = 460.5

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, 60025-06-1, 1-(4,6-Dichloropyrimidin-5-yl)ethanone.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/140947; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 875251-47-1 , The common heterocyclic compound, 875251-47-1, name is 2-(Pyrimidin-5-yl)ethanol, molecular formula is C6H8N2O, 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.

[0715] Synthesis of 5-(2-chloroethyl) pyrimidine: [0716] To a stirred solution of 2-(pyrimidin-5-yl) ethanol (20 mg, 0.16 mmol) in CH2CI2 (4 mL) under argon atmosphere was added sulfurous dichloride (0.02 mL, 0.32 mmol) at 0 C; heated to 50 C and stirred for 4 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mass was cooled to room temperature and pH was adjusted to ~8 using saturated NaHC03 solution( 5 mL) and the compound was extracted with CH2CI2 (2 x 10 mL). The combined organic extracts were dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 2% MeOH/ CH2C12 to afford 5-(2-chloroethyl) pyrimidine (18 mg, 77%) as colorless syrup. [0717] 1H-NMR (CDC13, 400 MHz): delta 9.16 (s, 1H), 8.66 (s, 2H), 3.78 (t, 2H), 3.12 (t, 2H); LC-MS: 97.54%; 143 (M++l); (column; Xbridge C-18, 50 3.0 mm, 3.5 mupiiota); RT 1.80 min. 0.05% TFA (aq.): ACN; 0.8 mL/min); UPLC (purity): 99.22%; (column: Acquity BEH C-18, 50 x 2.1 mm, 1.7 mu); RT 1.15 min. ACN : 0.025% TFA (Aq); 0.5 mL/min. (IP12060335); TLC: 10% MeOH/ CH2C12 (Rf: 0.7).

The synthetic route of 875251-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 34253-03-7, 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. 34253-03-7, name is Methyl pyrimidine-2-carboxylate. A new synthetic method of this compound is introduced below.

Pyrimidin-2-ylmethanol (12):To a stirred solution of ester 11 (0.43 g, 3.09 mmol) in EtOH (30 mL), cooled to 0C, NaBH4 (0.114 g, 3.09 mmol) was added and stirred for 2 h. After consumption of the starting material (by TLC), the reaction was quenched with cold water and concentrated under vacuo to give the crude material which was purified by silica gel column chromatography (MeOH/CH2Cl2 1 :49) to afford alcohol 12 (0.145 g, 37%) as syrup.TLC: 10% MeOH/CHCl3 (Rf: 0.3)1H NMR (500MHz, CDC13): delta 8.75 (d, J = 5.5 Hz, 2H), 7.26-7.22 (m, 1H), 4.85 (s, 2H).Mass (ESI): 111.1 [M++l].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,34253-03-7, Methyl pyrimidine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; THERACRINE, INC.; SUN, Lijun; BARSOUM, James; WESTER, Ronald; WO2013/13238; (2013); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 206564-00-3, 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. 206564-00-3, name is 4-(2-Furyl)pyrimidin-2-amine. A new synthetic method of this compound is introduced below.

General procedure: 4-p-Tolylpyrimidin-2-amine (3a) (1.0 equiv), N-chlorosuccinimide (1.1 equiv) and benzoyl peroxide (0.2 equiv) were dissolved in acetonitrile and stirred at 80 C for 6 h. The reaction mixture was cooled to room temperature, then the solvent was removed in vacuo. The crude product was purified by silica gel column with acetone/petroleum ether (v/v, 1:5) as eluent to obtain 4a. Using the same procedure described above for the other compounds exception of 6a-6c under a lower reaction temperature (40 C).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,206564-00-3, 4-(2-Furyl)pyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Article; Chen, Wei; Li, Yuxin; Zhou, Yunyun; Ma, Yi; Li, Zhengming; Chinese Chemical Letters; vol. 30; 12; (2019); p. 2160 – 2162;,
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. 213745-17-6, name is 4-Chloro-7-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Quality Control of 4-Chloro-7-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

1 C. 4-Chloro-7-cvclopentyl-7H-pyrrolof2, 3-dl vrimidine-5-carboxvlic acid; Starting material (1B, 10 g, 29 mmole) was taken in 500 mL DMF and 100 mL H20 together with palladium acetate (0.32 g, 1.4 mmole). The reaction mixture was stirred in a pressure reactor at 50 C under 100 psi carbon monoxide for 6.5 h and room temperature for 16 h. The reaction mixture was then concentrated and residue triturated with 100 mL of 1: 1 EtOAc/Ch2CI2 followed by 50 mL CH2CI2. The solid was collected after filtration and dried over P205 to furnish 21 g of an off-white solid. This solid was then triturated with a mixture of formic acid/H20 (21 mU5 mL). The solid collected after filtration and drying over P205 furnished 6.5 g of 1 C (m/z 265.1, retention time 2.5 min. with HPLC method 1).

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, 213745-17-6, 4-Chloro-7-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2005/47289; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 830346-47-9, 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 830346-47-9 as follows.

Bromine (3.2 g) was added to a solution of 1-(2-fluoro-6-(trifluoromethyl)benzyl)- 6-methylpyrimidine-2,4(1H,3H)-dione (6.0 g, 0.019 mmol) in acetic acid and stirred for 3 h at ambient temperature. Residue obtained was filtered and filtrate was diluted with ethyl acetate. The ethyl acetate layer was washed with sat. NaHCO3 solution. Organic layer was separated, washed with Na2S2O3 solution and then concentrated to give titled solid material (6.6 g, 87 percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,830346-47-9, its application will become more common.

Reference:
Patent; LUPIN LIMITED; SULAKE, Rohidas, Shivaji; SHINDE, Sagar, Raosaheb; SIYAN, Rajinder, Singh; BHISE, Nandu, Baban; SINGH, Girij, Pal; (22 pag.)WO2018/198086; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 43088-67-1, 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. 43088-67-1, name is 4-Chloro-5-methylthieno[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine (35 mg), 5,6-dimethyl-[2,2′]bipyridinyl-3-ol (38 mg), and 4-dimethylaminopyridine(69 mg) were dissolved in dimethylsulfoxide (1 ml). Cesium carbonate (185 mg) was added to the solution, and the mixture was stirred at 130C overnight. The reaction mixture was cooled to room temperature, and water was added thereto. 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 (46 mg, yield 70%). 1H-NMR (CDCl3, 400 MHz): delta 2.41 (s, 3H), 2.56 (d, J = 1.2 Hz, 3H), 2.63 (s, 3H), 7.02 (d, J = 0.7 Hz, 1H), 7.11 (dd, J = 6.1, 6.3 Hz, 1H), 7.46 (s, 1H), 7.66 (dd, J = 7.6, 7.8 Hz, 1H), 7.89 (d, J = 8.1 Hz, 1H), 8.34 (d, J = 4.1 Hz, 1H), 8.44 (s, 1H) Mass spectrometric value (ESI-MS, m/z): 371 (M+Na)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,43088-67-1, 4-Chloro-5-methylthieno[2,3-d]pyrimidine, and friends who are interested can also refer to it.

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