Pyrimidines

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. 145783-15-9, name is 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine. A new synthetic method of this compound is introduced below., Safety of 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine

4,6-Dichloro-2-(propylthio)pyrimidin-5-amine (0.5 g, 2.1 mmol) was dissolved in methanol (2 mL) and supplemented with te/t-butylamine (460.0 mg, 6.3 mmol). The reaction mixture was introduced in a sealed vessel and heated at 100C for 24 h. After concentration of the reaction mixture to dryness under vacuum, the residue was purified by silica gel column chromatography. Yield: 88%. Melting point: 88-89C. *H NMR (DMSO -d6) d 0.95 (t, J=7.3 Hz, 3H, SCH2CH2C/ ,), 1.43 (s, 9H, NHC(C/ ,)3), 1.62 (h, J=7.3 Hz, 2H, SCH2CH2CH3), 2.95 (t, J=7.3 Hz, 2H, SCH2CH2CH3), 4.91 (bs, 2H, NH2), 6.19 (s, 1H, NHC(CH3)3). 13C NMR (DMSO -d6) d 13.3 (SCH2CH2CH3), 22.9 (SCH2CH2CH3), 28.5 (NHC(CH3)3), 31.9(SCH2CH2CH3), 51.9 (NHC(CH3)3), 120.3 (C-5), 137.6 (C-6), 152.1 (C-4), 154.5 (C-2).

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, 145783-15-9, 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine.

Reference:
Patent; UNIVERSITE DE LIEGE; LANCELLOTTI, Patrizio; OURY, Cecile; PIROTTE, Bernard; (140 pag.)WO2019/158655; (2019); A1;,
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Application of 4270-27-3, 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. 4270-27-3, name is 6-Chloropyrimidine-2,4(1H,3H)-dione, molecular formula is C4H3ClN2O2, 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: 6-Chloropyrimidine-2,4(1H, 3H)-dione derivatives 1 (1.0 mmol) and N-hydroxyformimidoyl chloride derivatives 2 (1.2 mmol) were combined and dissolved in methanol (15mL), followed by the addition of triethylamine (3.0 mmol). Subsequently, the reaction mixture was stirred in a round-bottom flask (25mL) at room temperature for 5h. After completion of the reaction as indicated by TLC, the mixture was evaporated by rotary evaporator, extracted with ethyl acetate, dried over Na2SO4, then concentrated and purified by flash column chromatography (PE/EA=5:1) to yield compounds 3a-t.

According to the analysis of related databases, 4270-27-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jiang, Kun-Ming; Jin, Yi; Lin, Jun; Tetrahedron; vol. 73; 47; (2017); p. 6662 – 6668;,
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Related Products of 1032452-86-0, 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. 1032452-86-0, name is 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole, molecular formula is C13H10ClN3, 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.

4-Methylbenzenesulfonic acid hydrate (8.7 g) was added in one portion to 3-(2- chloropyrimidin-4-yl)-1-methylindole (9.3 g) and 4-fluoro-2-methoxy-5-nitroaniline (7.1 g) in nbutanol (200 mL). The resulting mixture was stirred at reflux for 1 h. The mixture was cooled to room temperature. The precipitate was collected by filtration, washed with n-butanol (50 mL), and dried under vacuum to afford N-(4-fluoro-2-methoxy-5-nitrophenyl)- 4-(1- methylindol-3- yl)pyrimidin-2-amine as a yellow solid (CompoundS, 15.5 g).

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 1032452-86-0, 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole.

Reference:
Patent; NEUFORM PHARMACEUTICALS, INC.; CHAORAN, Huang; CHANGFU, Cheng; (85 pag.)WO2017/117070; (2017); A1;,
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Application of 1004-39-3, 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.1004-39-3, name is 4,6-Diaminopyrimidine-2-thiol, molecular formula is C4H6N4S, molecular weight is 142.18, as common compound, the synthetic route is as follows.

General procedure: DBU (0.33 ml, 2.2 mmol) was added dropwise at roomtemperature to a stirred suspension of the respective thiol2a-n (2.2 mmol) in anhydrous MeCN (4 ml). The obtainedmixture was stirred for 15 min and then furoxan 1d (0.34 g,1.0 mmol) was added. The reaction mixture was furtherstirred for 48-120 h until complete conversion of thestarting furoxan 1d (control by TLC, eluent CHCl3). Thereaction mixture was then diluted with H2O (20 ml). The precipitate formed was filtered off, carefully washed withwater, 0.75 N NaOH, then again with water, acetonitrile(~1 ml), and air-dried.

The chemical industry reduces the impact on the environment during synthesis 1004-39-3, I believe this compound will play a more active role in future production and life.

Reference:
Article; Fershtat, Leonid L.; Epishina, Margarita A.; Kulikov, Alexander S.; Struchkova, Marina I.; Makhova, Nina N.; Chemistry of Heterocyclic Compounds; vol. 51; 2; (2015); p. 176 – 186; Khim. Geterotsikl. Soedin.; vol. 51; 2; (2015); p. 176 – 186,11;,
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Synthetic Route of 4595-59-9 , The common heterocyclic compound, 4595-59-9, name is 5-Bromopyrimidine, molecular formula is C4H3BrN2, 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.

Example 3 N-((1R,2R)-2-Hydroxy-cyclohexyl)-6-(2-pyrimidin-5-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinamidea) 5-Trimethylsilanylethynyl-pyrimidine; Tetrakis(triphenylphosphine)palladium(O) (727 mg, 0.6 mmol) was added to a stirred, degassed suspension of 5-bromopyrimidine (5.0 g, 31.4 mmol) and copper(I)iodide (120 mg, 0.6 mmol) in toluene and diisopropylamine (1:1, 200 ml) under nitrogen. The reaction mixture was heated to 60 C., trimethylsilylacetylene (4.89 ml, 34.6 mmol) was added and the reaction mixture was stirred for 3 hours at 60 C.. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate (200 ml) and washed with saturated aqueous ammonium chloride solution (3¡Á100 ml). The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (5% ethyl acetate/heptane) to give 5-trimethylsilanylethynyl-pyrimidine as a pale brown solid, 4.71 g (85% yield). LC at 215 nm; Rt 2.07: 88%, m/z (ES+): 177 (M+H).

The synthetic route of 4595-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hebeisen, Paul; Roever, Stephan; US2008/70931; (2008); A1;,
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Application of 10244-24-3, 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 10244-24-3 as follows.

Example 8: Preparation of Trianion of 5-bromo-4-(trifluoromethyl)pyridin-2-amine using 3.5 Equivalents of Isopropylmagnesium chloride, lithium chloride complexA reactor was charged with 5-bromo-4-(trifluoromethyl)pyridin-2-amine (1.000 g, 4.149 mmol) and tetrahydrofuran (7.72 ml). The mixture was sitrred for 10 minutes. The mixture was cooled to 0 C within 30 minutes. lsopropylmagnesiumcloride lithium chloride 1 .3M in THF (6.383 ml,8.298 mmol) was continuously added within a time period of 1.5 hours at 0 C. An additional1.5 equivalents of isopropylmagnesiumcloride lithium chloride 1 .3M in THF (4.788 ml, 6.224 mmol) was continuously added within a time period of 1 .5 hours at 0 C. An additional 0.5 equivalents of isopropylmagnesiumcloride lithium chloride 1 .3M in THF (1 .596 ml, 2.075 mmol) was continuously added within a time period of 1 hour at 0 C. The product was the trianion of 5-bromo-4-(trifluoromethyl)pyridin-2-amine, as determined by HPLC and LCMS.Example 9: Preparation of 5-(2,6-Di-4-morpholinyl-4-pyrimidin-4-yl)-4- (trifluoromethyl)pyridin-2-amine (Compound A)The compound 4,4?-(6-chloropyrimidine-2,4-diyl)dimorpholine (0.40g, 1.405 mmol), 1,1?- Bis(diphenylphosphino)ferrocene (0.040g, 0.070 mmol) and Palladium acetate (0.016g, 0.070 mmol) and 2 mL of tetrahydrofuran were placed in an inertized reactor. The reactor is evacuated to 100 mbar and flushed with nitrogen two times. lsopropylmagnesiumcloride lithium chloride 1 .3M in THF (1.405 mmol) was added at 30 C followed by an equivalent amount of the trianion of 5-bromo-4-(trifluoromethyl)pyridin-2-amine (1.405 mmol). The suspension was stirred for 0.5 hours. The product was 5-(2,6-Di-4-morpholinyl-4-pyrimidin-4-yl)-4- (trifluoromethyl)pyridin-2-amine, as determined by HPLC and LCMS.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10244-24-3, its application will become more common.

Reference:
Patent; NOVARTIS AG; FLUBACHER, Dietmar; BIERI, Nicole; ACEMOGLU, Murat; MICHEL, Pascal; MOSE, Rasmus; STETTLER, Hans; TESTA, Maria Caterina; BROZIO, Joerg; SCHAEFER, Frank; WO2014/64058; (2014); A1;,
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Electric Literature of 1780-33-2, Adding some certain compound to certain chemical reactions, such as: 1780-33-2, name is 4,6-Dichloro-2,5-dimethylpyrimidine,molecular formula is C6H6Cl2N2, 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 1780-33-2.

Preparation F (6–Chloro-2,5-dimethylpyrimidin-4-yl)-(2,4,6-trimethylphenyl)-acetonitrile To a solution of mesitylacetonitrile (0.900 g, 5.65 mmol) in 8 ml dry THF was added sodium hydride (60percent in oil, 0.250 g, 6.21 mmol) and the mixture was stirred at room temperature for 40 minutes. 2,5-Dimethyl-4,6-dichloropyrimidine (1.000 g, 5.65 mmol) was added and the resulting mixture was heated at reflux for 5 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 1.800 g of a yellow oil. The oil residue was purified through silica gel column chromatography using 10percent ethyl acetate in hexane as eluent to give 0.986 9 (58.3percent) of the title compound as a white solid, mp 100-102¡ã C. 1 H NMR (CDCl3) delta6.86 (s, 2H), 5.60 (s, 1H), 2.69 (s, 3H), 2.25 (s, 3H), 2.18 (s, 6H), 1.92 (s, 3H) ppm.

According to the analysis of related databases, 1780-33-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US5962479; (1999); A;,
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Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1193-21-1, name is 4,6-Dichloropyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 1193-21-1

298 mL of methanol was added to 387 mL (7.98 mols) of hydrazine monohydrate, cooled at 10C (inside temperature), and 149 g (1.00 mol) of 4,6-dichloropyrimidine was gradually added to the mixture liquid (at inside temperature of not higher than 20C), then the ice bath was removed, and this was restored to room temperature and stirred at the temperature for 30 minutes. Afterwards, this was further heated up to 60C (inside temperature), and stirred at the temperature for 5 hours. After the reaction, 750 mL of water was added thereto, and cooled with ice to 8C (inside temperature), and the precipitated crystal was collected through filtration, washed with water poured thereto, and then with isopropanol poured thereto. This was dried at room temperature for 36 hours to give 119 g of the intermediate (c) (white powder, yield 84.5%). The NMR data of the obtained intermediate (c) are as follows: 1H-NMR (300 MHz, d-DMSO): 7.80 (s, 1H), 7.52 (s, 2H), 5.98 (s, 1H), 4.13 (s, 4H)

The synthetic route of 1193-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM Corporation; EP2228409; (2010); A2;,
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Adding a certain compound to certain chemical reactions, such as: 5466-43-3, 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[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, Recommanded Product: 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, blongs to pyrimidines compound. Recommanded Product: 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine

Example 22. Preparation of Compound Nos. 142, 142a and 142b Step 3. To a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine (1.5 g, 7.90 mmol) in isopropanol (15 mL) was added Nu,Nu-diisopropylethyl amine (2.18 mL, 12.64 mmol) followed by 5-(tert-butyl)-lH-pyrazol-3-amine (1.32 g, 9.48 mmol). The reaction mixture was refluxed at 100 C for 16 h. The reaction mixture was concentrated under vacuum to get oily residue which was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with water (3×60 mL) and dried over anhydrous sodium sulfate. Removal of solvent afforded solid crude was triturated with ether (20 mL) to get N-(5-(tert-butyl)-lH-pyrazol-3-yl)-2-chloro-6,7-dihydro-5H- cyclopenta[d]pyrimidin-4-amine (720 mg, 31.44%).

The synthetic route of 5466-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; CHAKRAVARTY, Sarvajit; RAI, Roopa; GREEN, Michael, John; ANSARI, Amantullah; AGARWAL, Anil, Kumar; (216 pag.)WO2016/3827; (2016); A2;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide, the common compound, a new synthetic route is introduced below. Computed Properties of C5H4ClN3O

To a solution of 0.07 g (0.19 mmol, 1.0 eq.) of(S)-1-amino-N-(3-chloro-4-fluorophenyl)-7- fluoro-2,3 -dihydro- 1H-indene-4-carboxami de hydrochloride (Vild) and 30 mg (0.21 mmol, 1.10 eq.) of 2-chloropyrimidine-4-carboxamide in 2 mL of NIVIP was added 0.07 ml (0.39mmol, 2.0 eq.) of N,N-diisopropylethylamine, and the mixture was subjected to microwave irradiation maintaining a reaction temperature of 130 C for 1 h. The mixture was diluted with 50 mL of ethyl acetate and washed 2 x 20 ml of water followed by 10 mL of brine. The organic phase was dried (Na2SO4), filtered and the solvent was removed in vacuo. The residue was purified by flash chromatography (Si02, eluting with a linear gradient of 0-30%ethyl acetate/hexanes) to provide 24 mg (0.05 mmol, 29%) of(S)-2-((4-((3-chloro-4- fluorophenyl)carbamoyl)-7-fluoro-2,3 -dihydro- 1H-inden- 1 -yl)amino)pyrimidine-4- carboxamide (104). LCMS: m/z found 444. 1/446.1 [M+H]. HPLC: RT = 4.13 mm (Method A); ?H NIVIR (300 MFIz, Methanol-d4) 8.50 (d, 1H), 7.93 (dd, 1H), 7.61-7.72 (m, 1H), 7.50- 7.60 (m, 1H), 7.16-7.28 (m, 2H), 7.03 (t, 1H), 5.88-5.95 (m, 1H), 3.07-3.48 (m, 2H), 2.55-2.66(m, 1H),2.10(m, 1H).

The synthetic route of 22536-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; COLE, Andrew, G.; DORSEY, Bruce, D.; KAKARLA, Ramesh; KULTGEN, Steven; QUINTERO, Jorge; (353 pag.)WO2018/172852; (2018); A1;,
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