Tag: M.W:100-200

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. 919278-72-1, name is 5-Methyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one. A new synthetic method of this compound is introduced below., Product Details of 919278-72-1

A mixture of 5-methyl-5H-pyrrolo [3, 2-d]pyrimidin-4-ol(489 mg, 3.28 mmol), 1- (bromomethyl) -4-nitrobenzene (1.06 g, 4.92 mmol), potassium carbonate (1.36 g, 9.84 mmol), sodium iodide (98.3 mg, 0.656 mmol) and N,N-dimethylformamide (7 mL) was stirred at 500C for 15 hr. The reaction mixture was diluted with water, and extracted with ethyl acetate (chi3) . The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (ethyl acetate/hexane=30/70->100/0) to give the title compound (489 mg, 52%) as a yellow solid. 1H-NMR (DMSO-ds, 300 MHz) delta 3.98 (3H, s) , 5.30 (2H, s) , 6.35 -6.36 (IH, m) , 7.41 (IH,- d, J = 2.7 Hz), 7.54 (2H, d, J = 8.9Hz), 8.20 (2H, d, J = 8.9 Hz), 8.29 (IH, s) .

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, 919278-72-1, 5-Methyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/4749; (2007); 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

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;,
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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

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

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

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

Electric Literature of 1245506-61-9, 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. 1245506-61-9, name is 2-Chloro-5-methoxy-4-methylpyrimidine. A new synthetic method of this compound is introduced below.

To a -78 C solution of Intermediate 3B (1.60 g, 10.09 mmol) in DCM (20 mL) was added BBr3 (3.82 mL, 40.4 mmol) dropwise. The reaction mixture was allowed to slowly warm to RT and stirred for 16 h at RT, then was cautiously quenched with satd aq. NaHC03 (pH adjusted to ~4) and partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (2x); the combined organic layers were dried (MgS04) and concentrated in vacuo. The crude product was chromato graphed (40 g S1O2; continuous gradient from 0-100% EtOAc in Hexane over 15 min) to afford the title compound (1.33 g, 9.20 mmol, 91 % yield) as a white solid. NMR (400 MHz, DMSO- d6) d 10.63 (s, 1H), 8.11 (s, 1H), 2.34 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1245506-61-9, 2-Chloro-5-methoxy-4-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; WANG, Ying; CHENG, Peter Tai Wah; LI, Jun; WALKER, Steven J.; (147 pag.)WO2019/126089; (2019); 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 13877-55-9, name is 7-Hydroxypyrazolo[4,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

[0507] Procedure: To a stirred solution of 1H-pyrazolo[4,3-d]pyrimidin-7-ol (0.2 g, 1.47 mmol) in thionyl chloride (4.2 mL) were added DMF (0.2 mL). Reaction mixture was stirred for 1h at 90 oC. The Progress of the reaction was monitored by TLC. Reaction mixture was diluted with ethyl acetate (50 mL) washed with sat. sodium bicarbonate (30 mL) followed by brine (30mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressureto afford 7-chloro-1H-pyrazolo[4,3-d]pyrimidine as pale yellow solid (0.05 g, 22%). LC-MS (ES) m/z =168.9 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 13877-55-9.

Reference:
Patent; MAVUPHARMA, INC.; GALLATIN, William Michael; ODINGO, Joshua; DIETSCH, Gregory N.; FLORIO, Vincent; VENKATESHAPPA, Chandregowda; DURAISWAMY, Athisayamani Jeyaraj; (273 pag.)WO2019/46778; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 69205-79-4, 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. 69205-79-4, name is 2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, molecular formula is C7H5N5O, 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.

In a dry round bottomed flask under an atmosphere of argon, trityl chloride (1.20 g, 4.28 mmol) was added to a solution of 2-amino-4,7-dihydro-4-oxo-3A/- pyrrolo[2,3-d]pyrimidine-5-carbonitrile (0.50 g, 2.85 mmol) in dry pyridine (29 ml_). The mixture reaction was heated at 90 C for 48 h. The reaction mixture was concentrated under reduced pressure then absorbed on silica gel and purified by flash chromatography on silica gel eluting with dichloromethane/MeOH with a gradient starting at 2% of MeOH and rising to 10%. The desired compound was obtained as a brown solid (0.63 g, 1.5 mmol, 53% yield). Procedure based on Olgen 2008. deltaEta (400 MHz, DMSO-de) delta 11.80 (br s, 1H); 10.64 (br s, 1H), 7.56 (s, 1H), 7.41(s, 1H), 7.29-7.28 (m, 12H), 7.23-7.17 (m, 3H), 5.73 (s, 1H). HRMS (m/z ESI+) : C26Hi8N50 [M-H]+ Found 416.1514 Requires: 416.1511.

According to the analysis of related databases, 69205-79-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH, NEAR DUBLIN; SOUTHERN, John, Michael; CONNON, Stephen, J.; (37 pag.)WO2016/50804; (2016); A1;,
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Pyrimidine – Wikipedia