Pyrimidines

Synthetic Route of 7752-78-5 ,Some common heterocyclic compound, 7752-78-5, molecular formula is C5H5BrN2, 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 10-L 4-neck round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 5-bromo-2-methylpyrimidine (184 g, 1.06 mol) and B (i-PrO)3(240 g, 1.28 mol) in THF/toluene (3/3 L) . This was followed by the dropwise addition of a 2.5 M solution of n-BuLi (510 mL, 1.28 mol) with stirring at -78 . The resulting solution was stirred for 1 h at -78 , then quenched by the addition of 200 mL of aqueous NH4Cl. The organic phase was dried and concentrated under vacuum. The aqueous phase was adjusted to pH 4 with AcOH. The solid was collected by filtration and dried in an oven under reduced pressure providing (2-methylpyrimidin-5-yl) boronic acid.

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. 7752-78-5, 5-Bromo-2-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACHAB, Abdelghani Abe; CHRISTOPHER, Matthew P.; FRADERA LLINAS, Francesc Xavier; KATZ, Jason D.; METHOT, Joey L.; ZHOU, Hua; XU, Shimin; FU, Jianmin; FU, Ning; LI, Yabin; WANG, Xichao; (228 pag.)WO2017/166104; (2017); A1;,
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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. 89792-07-4, name is 2-Methyl-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Formula: C7H7N3

2-methyl-7H-pyrrolo[2,3-d]pyrimidine (426 mg, 3.2 mmol) was dissolved in DMF (54 mL) cooled in an ice bath and treated with N-bromosuccinimide (569 mg, 3.2 mmol) portionwise under nitrogen. The resulting mixture was stirred for 20 minutes, allowed to warm to room temperature and stirred for 10 minutes. The reaction was quenched by the addition of CH3OH (5 mL) and the solvent removed under reduced pressure. The residue was purified by silica flash column chromatography using a heptane to ethyl acetate gradient. The desired fractions were collected and the solvent was removed under reduced pressure to afford 5-bromo-2-methyl-7H-pyrrolo[2,3-d]pyrimidine, 19.

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, 89792-07-4, 2-Methyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Janssen Sciences Ireland UC; JONCKERS, Tim Hugo Maria; MC GOWAN, David Craig; RABOISSON, Pierre Jean-Marie Bernard; EMBRECHTS, Werner Constant Johan; GUILLEMONT, Jerome Emile Georges; (42 pag.)US2017/253600; (2017); A1;,
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Application of 5305-40-8, 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 5305-40-8, name is 4,6-Dichloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To the solution of 4,6-dichloropyrimidine-5-carbaldehyde 2 (1.0g, 5.6mmol) in methanol (20mL) at-65C, triethylamine (0.97mL) was added. A solution of hydrazine monohydrate (0.274mL 1.0 eq.) in methanol (10mL) was slowly dripped into above stirred solution by using a constant-pressure dropping funnel. The mixture was allowed to warm to room temperature and stirred for 2-3h. The reaction mixture was concentrated in vacuo and crude product was diluted with water (20mL), and extracted with EtOAc (60mL¡Á3). The combined organic layer was washed with saturated solution of NaCl (60mL¡Á3), dried over MgSO4 and concentrated to give compound 3 (0.602g, yield: 68.9%.) 1H NMR (400MHz, deuteriated dimethyl sulfoxide (DMSO-d6)) delta 14.51 (s, 1H), 8.84 (s, 1H), 8.45 (s, 1H). ESI-MS m/z: 153.00 [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 5305-40-8, 4,6-Dichloropyrimidine-5-carbaldehyde.

Reference:
Article; Wang, Yuanyuan; Wan, Shanhe; Li, Zhonghuang; Fu, Yu; Wang, Guangfa; Zhang, Jiajie; Wu, Xiaoyun; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 210 – 228;,
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Related Products of 23956-12-9, Adding some certain compound to certain chemical reactions, such as: 23956-12-9, name is 5-(2-Hydroxyethyl)pyrimidine-2,4(1H,3H)-dione,molecular formula is C6H8N2O3, 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 23956-12-9.

Mixture of 2 (2.75 g, 17.61 mmol) and acetic anhydride (14.1 mL, 0.15 mol) in anhydrous pyridine (25 mL) was refluxed for 1 h, then water (20 mL) was added and solvent was removed under reduced pressure. Co-evaporation of oily residue with toluene (2 x 30 mL) gave crude product which was purified by column chromatography (CH2Cl2 : CH3OH = 20 :1) to give white crystals of 4 (3.31 g, 95 %, m.p.= 205 – 207 C). 1H-NMR: 11.08 (1H, s, NH-3), 10.72 (1H, s, NH-1), 7.32 (1H, s, H-6), 4.07 (2H, t, J = 6.73 Hz, H-2′), 2.48 (2H, t, J = 6.69 Hz, H-1′), 1.99 (3H, s, CH3). 13C-NMR: 170.72 (C=O), 159.60 (C-4), 156.13 (C-2), 151.28 (C-6), 115.17 (C-5), 62.75 (C-2′), 24.32 (C-1′), 21.13 (CH3). ESI-MS 199 [M+H]+. Anal. calcd. For C8H10N2O4: C 48.48, H 5.09. Found: C 48.39, H 5.11.

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. 23956-12-9, 5-(2-Hydroxyethyl)pyrimidine-2,4(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kraljevi?, Tatjana Gazivoda; Klika, Mateja; Kralj, Marijeta; Martin-Kleiner, Irena; Jurmanovi?, Stella; Mili?, Astrid; Padovan, Jasna; Rai?-Mali?, Silvana; Bioorganic and Medicinal Chemistry Letters; vol. 22; 1; (2012); p. 308 – 312;,
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Reference of 919116-36-2, Adding some certain compound to certain chemical reactions, such as: 919116-36-2, name is 4-Chloro-2-(methylthio)-5-(trifluoromethyl)pyrimidine,molecular formula is C6H4ClF3N2S, 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 919116-36-2.

To a reaction vessel charged with 4-chloro-2-(methylthio)-5-(trifluoromethyl)pyrimidine (1.98 g, 8.66 mmol) and sodium iodide (3.89 g, 26.0 mmol) was added hydriodic acid (28 mL, 57 %). The vessel was sealed and the mixture allowed to stir for 48h at rt before being poured into water. The resulting precipitate was collected by vacuum filtration, washed with sat. aq. NaHC03 sol. and dried under vacuum to give the title compound as a pale yellow solid (1.46 g, 53 %). LCMS (Method 1 ) Rt 3.003 min.

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. 919116-36-2, 4-Chloro-2-(methylthio)-5-(trifluoromethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIONOMICS LIMITED; HARVEY, Andrew John; RIPPER, Justin Anthony; HUFF, Belinda Cheryl; PAUL, Dharam; WO2015/123722; (2015); A1;,
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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. 105742-66-3, name is 4,5-Dichloro-2,6-dimethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H6Cl2N2

General procedure: Compound 5 was synthesized as described.33 Compounds 6 and 7were synthesized in our previous work.34 Compounds 4 (5 mmol), 7(5 mmol) and anhydrous potassium carbonate (5 mmol, 0.69 g) wereadded to a mixed solvent of dimethyl formamide (20 mL) and water(10 mL), and then refluxed for 2-4 h. The progress was monitored byTLC. After the reaction was complete, the reaction solution was pouredinto saturated saline and extracted with ethyl acetate (3¡Á80 mL). Theextract was dried, filtered, and the solvent was removed under reducedpressure to give a crude product. Recrystallization from the mixedsolvent of petroleum ether and ethyl acetate gave pure target compoundsO1-17 (Scheme 2). The yields, physical properties, and 1HNMR, GC/HPLC-MS, elemental analyses of the target compounds are asfollows:Data for O1: yield, 75%; purity, 95.5%; yellow solid; mp,101.9-103.9 C. 1H NMR (CDCl3) delta 2.450 (s, 3H, CH3), 2.531 (s, 3H,CH3), 4.663 (q, J=0.6 Hz, 2H, CH2), 5.899 (s, 1H, NH), 7.443-7.491(m, 3H, Ph H), 7.664 (t, J=0.9 Hz, 1H, oxzole H), 8.003-8.049 (m, 2H,Ph H); GC-MS M+=314, base peak 182. Anal. Calcd(%) forC16H15ClN4O: C, 61.05; H, 4.80; N, 17.80. Found: C, 61.07; H, 4.79; N,17.83.

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, 105742-66-3, 4,5-Dichloro-2,6-dimethylpyrimidine.

Reference:
Article; Yan, Zhongzhong; Liu, Aiping; Ou, Yingcan; Li, Jianming; Yi; Zhang, Ning; Liu, Minhua; Huang, Lu; Ren, Jianwei; Liu, Weidong; Hu, Aixi; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3218 – 3228;,
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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. 211244-81-4, name is 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one, the common compound, a new synthetic route is introduced below. Safety of 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

[00495] To a suspension of sodium hydride (60% in mineral oil, 204 mg, 5.1 mmol) in anhydrous dimethylformamide (12 mL) was added a solution of 2-methylsulfanyl-8H-pyrido[2,3- d]pyrimidin-7-one (1) (500 mg, 2.59 mmol) in anhydrous dimethylformamide (5 mL) then lithium bromide (590 mg, 6.79 mmol) at 0-5 C. After 30 min, a solution of 1 -chloromethyl-2- ethanesulfonyl-benzene (30) (743 mg, 3.39 mmol) in anhydrous dimethylformamide (7 mL) was added slowly and stirring was continued at room temperature for 18 h. The resulting mixture was poured into ice water (150 g) and extracted with ethyl acetate (5 x 20 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated. The residue was purified by ISCO using n-hexane: ethyl acetate (1 :0?1 : 1) as eluent. The title compound (188 mg, 0.50 mmol, 19%) was obtained as a light yellow solid. ESMS m/z 376 (M+H)+; 1H NMR (400 MHz, CDC13) delta ppm 8.69 (s, 1H) 8.02 – 8.08 (m, 1H) 7.72 (d, J= 9.5Hz, 1H) 7.39 – 7.48 (m, 2H) 6.79 – 6.88 (m, 1H) 6.69 (d, J= 9.5Hz, 1H) 6.03 (s, 2H) 3.57 (q, J= 7.4Hz, 2H) 2.47 (s, 3H) 1.40 (t, J= 7.4Hz, 3H).

The synthetic route of 211244-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio, G.; WO2013/86451; (2013); A2;,
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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.42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H2Cl2N4, molecular weight is 189, as common compound, the synthetic route is as follows.name: 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine

1-(4-{4-(3,6-dihydro-2H-pyran-4-yl)-1-[1-(pyridin-3-ylcarbonyl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}phenyl)-3-methylurea (Scheme 13)Example 5Step 14,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine, prepared according to Robins (J Am Chem. Soc. Vol. 79, 1957, 6407-6415) was reacted with 3,4-dihydro-2H-pyran and catalytic p-toluenesulfonic acid in ethyl acetate at 70 C. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. After concentration of organic layers, the crude material was purified by flash chromatography to provide 4,6-dichloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,42754-96-1, 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Wyeth; US2009/192176; (2009); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 289042-10-0, N-(5-((Diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, 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, Safety of N-(5-((Diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, blongs to pyrimidines compound. Safety of N-(5-((Diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide

Sodium bis (trimethylsilyl) amide (1 M in tetrahydrofuran, 23 mi) is added dropwise, AT-74C, to a suspension of the compound of formula (38) (12 g, 22.3 MMOL) in tetrahydrofuran (130 M .). STIRRING is carried out at-74C for 1 hour and then a solution of the compound of formula (40) (6.9 g, 26.8 MMOI) in toluene (28 ML) is added dropwise. Stirring is then carried out AT-74C for 1 hour, then warming to 10C over the course of 1 hour and stirring for a further 1 hour at that temperature. A mixture of acetic acid (2 ml) and water (8.4 ML) is added, at 10C, to the resulting yellow suspension and stirring is carried out at room temperature for 5 minutes. The tetrahydrofuran is then distilled off, and, at 40C, 45 ml of water are added to the reaction mixture and vigorous stirring is carried out for 5 minutes. The aqueous phase is separated off and a solution of sodium hydrogen carbonate (2.27 G) in water (45 ml) is added to the organic phase. Vigorous stirring is again carried out for 5 minutes and then the aqueous phase is removed again. The organic phase is diluted with 250 ML of toluene, washed successively with water and saturated sodium chloride solution and dried (using NA2SO4). The salt mixture is filtered off and the filtrate is concentrated by evaporation. The concentrated residue is then purified by column chromatography on silica gel (hexane: ethyl acetate 8: 1). 2.59 G (61 %) of the desired product (39) can be obtained in the form of colourless crystals. ‘H NMR (300 MHz, CDCI3) : 0.91-1. 08 (m, 1H) ; 1.20 (d, J = 6. 7 HZ, 6H); 1. 24 (S, 3H); 1. 38 (S, 9H); 1.41 (S, 3H); 1.41-1. 56 (m, 1 H) ; 2.21 (dd, J = 15. 2, 7. 9, 1 H) ; 2. 35 (dd, J = 15. 0, 5. 0 HZ, 1H) ; 3. 27-3. 37 (m, 1H) ; 3. 43 (S, 3H); 3.52 (S, 3H); 4.17-4. 24 (m, 1H) ; 4. 47-4. 53 (m, 1H) ; 5.43 (dd, J = 16.4, 5.5 Hz, 1H) ; 6.55 (dd, J = 16.1, 0.8 Hz, 1H) ; 7.24 (dd, J = 8.8, 8.8 HZ, 2H); 7.65 (dd, J = 8.8, 5.6 Hz, 2H). 13C NMR (75 MHz, CDCI3) : 18.7, 20.6, 20.7, 27.0, 29.0, 30.9, 32.0, 35.0, 41.3, 41.4, 64.8, 68.1, 79.6, 97.7, 113.7 (JCF = 21.7 Hz), 120.0, 122.0, 131. 0 (JCF = 8.4 Hz), 133.2 (JCF = 3.2 Hz), 136.3, 156.0, 162.0 (JCF = 249 Hz), 162.2, 168.8, 173.6.

The synthetic route of 289042-10-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CIBA SPECIALTY CHEMICALS HOLDING INC.; WO2004/103977; (2004); A2;,
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Adding a certain compound to certain chemical reactions, such as: 66131-68-8, 2-Chloro-N-methylpyrimidin-4-amine, 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, 66131-68-8, blongs to pyrimidines compound. category: pyrimidines

Into a 50-mL round-bottom flask, was placed 2-chloro-N-methylpyrimidin-4- amine (150 mg, 1.04 mmol, 1 equiv), tert-butyl 3-aminopiperidine-l-carboxylate (220 mg, 1.10 mmol, 1.05 equiv), trifluoroacetic acid (380 mg, 3.36 mmol, 3.00 equiv), IPA (5 mL). The resulting solution was stirred for 16 h at 90 C in an oil bath. The crude product was purified by Prep-HPLC C NH4HCO3. This resulted in 132.4 mg (61%) of N4-methyl-N2- (piperidin-3-yl)pyrimidine-2,4-diamine as a white powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,66131-68-8, its application will become more common.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (2017); A1;,
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