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. 100130-05-0, name is 5-Amino-2-(methylthio)pyrimidine-4-carboxylic acid. A new synthetic method of this compound is introduced below., name: 5-Amino-2-(methylthio)pyrimidine-4-carboxylic acid

EXAMPLE VI 4-Hydroxy-6-methylthiopyrimido[5,4-d]pyrimidine A mixture of 69 g of 5-amino-2-methylthiopyrimidine-4-carboxylic acid, 155 g of formamidine acetate and 300 ml of ethoxyethanol is heated to boiling for 2 hours. The reaction mixture is then cooled to 10 C., 250 ml of water are added, and the mixture is left to stand at 10 C. for one hour. It is then filtered with suction, washed with water and dried. Yield: 59 g (82% of theory), Melting point: >240 C., Rf: 0.63 (silica gel; methylene chloride/ethyl acetate/methanol=10:4:3). The following compound is obtained in analogy to Example VI:

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, 100130-05-0, 5-Amino-2-(methylthio)pyrimidine-4-carboxylic acid.

Reference:
Patent; Dr. Karl Thomae GmbH; US5977102; (1999); A;,
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Synthetic Route of 955368-90-8, Adding some certain compound to certain chemical reactions, such as: 955368-90-8, name is 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one,molecular formula is C9H10N4OS, 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 955368-90-8.

Preparative Example 1-1 Production of 2-allyl-6-(methylthio)-l-pyridin-2-yl-3H-pyrazolo[3,4-d]pyrimidin-3-one: 2.4 mL of Nu,Nu’-dimethylethylenediamine was added to 1,4-dioxane (50 mL) solution of 4.44 g of 2-allyl-6-(methylthio)-l,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one, 3.80 g of copper(I) iodide, 5.33 g of 2-iodopyridine and 3.80 g of potassium carbonate, and stirred overnight at 95C. The reaction liquid was cooled, aqueous ammonia was added thereto and extracted with ethyl acetate, washed with saturated saline water and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and crystallized with ethyl acetate to obtain 5.15 g of the entitled compound as a white solid. lH-NMR (400 MHz, CDCI3) delta: 8.94 (IH, s), 8.52 (IH, d, J=5.1 Hz), 7.90 (2H, d, J=3.5 Hz), 7.29-7.25 (IH, m), 5.68 (IH, ddt, J=17.0, 10.2, 6.3 Hz), 5.05 (IH, d, J=10.2 Hz), 4.91 (IH, d, J=17.0 Hz), 4.85 (IH, d, J=6.3 Hz), 2.58 (3H, s).

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. 955368-90-8, 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDREN’S HOSPITAL OF PHILADELPHIA; COLE, Kristina; MARIS, John; RUSSELL, Michael; BENITA, Yair; KUBICA, Jamie; SHUMWAY, Stuart Denham; WO2014/62454; (2014); A1;,
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Application of 10132-07-7, 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 10132-07-7, name is 4-Amino-2,6-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

2-(4-acetylpiperazin-1-yl)-6-chloropyrimidin-4-amine (4-3) 2,4-dichloro-6-aminopyrimidine 4-1 (0.5 g, 3.05 mmol) and triethyl-amine (0.617 g, 6.10 mmol) were dissolved in DMF and then 1-acetylpiperazine 4-2 (0.391 g, 3.10 mmol) was added as a solid and stirred for 2 hours. A precipitate was filtered off and discarded. The DMF was then evaporated off and to the residue was added ethyl acetate and DCM. The product was purified on silica gel (DCM:MeOH: NH4OH 98:2:0.2) which separated the two regioisomers. The desired product was the major product. 1H-NMR (CD3OD): 5.83 ppm (s, 1H); 3.79 ppm (m, 2H); 3.72 ppm (m, 2H); 3.60 ppm (m, 2H); 3.57 ppm (m, 2H); 2.14 ppm (s, 3H).

According to the analysis of related databases, 10132-07-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bilodeau, Mark T.; Hartman, George D.; Hoffman JR., Jacob M.; Sisko, John T.; Manley, Peter J.; Smith, Anthony M.; Tucker, Thomas J.; Lumma JR., William C.; Rodman, Leonard; US2002/137755; (2002); A1;,
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Application of 90349-23-8, 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. 90349-23-8, name is 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, molecular formula is C9H9N3O2, 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.

A solution of 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxylic acid 2 (300 mg, 1.56 mmol) in DMF (10 niL) at 0C was charged with HATU (894 mg, 2.35 mmol), DIPEA (0.82 mL, 4.70 mmol) and 4-amino phenol (205 mg, 1.88 mmol). Then, the reaction mixture was warmed to room temperature and stirred for 16 h. The reaction mixture was quenched with water (2 mL), extracted with ethyl acetate (3 X 10 mL), dried over Na2S04and concentrated in vacuo to provide a crude product that was then purified by FCC (eluent, 5% methanol in DCM) to afford N-(4-hydroxyphenyl)-5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxamide as an off-white solid (284 mg, 64%). NMR (400 MHz, DMSO-i) delta 9.92 (s, 1H), 9.26 (s, 1H), 8.58 (s, 1H), 7.51 (d, J=7.9 Hz, 2H), 7.16 (s, 1H), 6.77 (d, J=7.9 Hz, 2H), 2.76 (s, 3H), 2.68 (s, 3H). ES-MS m/z 283.15 (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 90349-23-8, 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse, Marie Josee; (139 pag.)WO2016/73895; (2016); A1;,
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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 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1211443-61-6

General procedure: To a suspension of 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (5) (586 mg, 2 mmol) in 20 mL 1,4-dioxane were added compound 3p-q (2 mmol), Pd(OAc)2 (11 mg, 0.05 mmol), BINAP (62 mg, 0.1 mmol) and Cs2CO3 (1.63 g, 5 mmol) and the flask was purged with Ar. Then the flask was sealed and the mixture was heated for 12 h at 100. The reaction was cooled to rt, the solvent was removed under reduced pressure, and the residue was purified by silica gel column to obtain 4p-q.

With the rapid development of chemical substances, we look forward to future research findings about 1211443-61-6.

Reference:
Article; Li, Yongtao; Guo, Qingxiang; Zhang, Chao; Huang, Zhi; Wang, Tianqi; Wang, Xin; Wang, Xiang; Xu, Guangwei; Liu, Yanhua; Yang, Shengyong; Fan, Yan; Xiang, Rong; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3231 – 3237;,
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Adding a certain compound to certain chemical reactions, such as: 1195-08-0, 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde, 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 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde, blongs to pyrimidines compound. Safety of 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

General procedure: To a solution of the pseudothiohydantoin 6a (139 mg, 1.2 mmol), and sodium acetate (328 mg, 4.0 mmol) in acetic acid (5 ml) was added 5-phenyl-2-furaldehyde 5a (172 mg,1.0 mmol) at 25C. The solution was refluxed at 135C for 12 h. The precipitate was filtered and washed with water and diethyl ether. The filter cake was dried under high vacuum to afford 230 mg (85%) of compound 7a as an orange solid.

The synthetic route of 1195-08-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jung, Michael E.; Ku, Jin-Mo; Du, Liutao; Hu, Hailiang; Gatti, Richard A.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 19; (2011); p. 5842 – 5848;,
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Electric Literature of 99420-75-4 ,Some common heterocyclic compound, 99420-75-4, molecular formula is C6H6N2O2, 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.

To a solution of 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24 mmol) in DMF (72.4 ml) was added 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24mmol), and N,0- dimethylhydroxylamine hydrochloride (0.777 g, 7.96 mmol). The mixture was cooled to 0 C and 1-propanephosphonic acid cyclic anhydride, 50 wt. % solution in EtOAc (9.21 ml, 14.48 mmol) was added droppwise. The mixture was allowed to warm to RT overnight. LCMS indicated complete conversion to product. The mixture was diluted with water, extracted with CHC13:IPA (3: 1) and washed with brine and NaHC03. The mixture was dried over Na2S04, concentrated in vacuo and purified by silica gel chromatography (0-100% heptane s:EtO Ac) to yield N-methoxy-N,5-dimethylpyrimidine- 2-carboxamide (0.7 g, 3.86 mmol, 53.4 % yield). NMR (500 MHz, CDC13) delta 8.61 – 8.69 (m, 2 H) 3.61 – 3.79 (m, 3 H) 3.27 – 3.47 (m, 3 H) 2.34 – 2.45 (m, 3 H). LCMS-ESI (pos.) m +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,99420-75-4, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; SHARMA, Ankit; (321 pag.)WO2018/93576; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 26032-72-4, 2,4-Dichloro-6-phenylpyrimidine, 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: 26032-72-4, blongs to pyrimidines compound. Recommanded Product: 26032-72-4

Step (i): Synthesis of (2-chloro-6-phenyl-pyrimidin-4-yl)-((R)-1-phenyl-ethyl)-amine To 2,4-dichloro-6-phenylpyrimidine (1.343 g, 6 mmol), dissolved in 30 mL methanol, was added DIEA (1.1 mL, 6 mmol) and was stirred for 23 min at about 20-35 C. under a nitrogen atmosphere. To this mixture was added (R)-(+)-alpha-methyl-benzylamine (0.76 mL, 6 mmol) and stirred for about 10-19 h. The mixture was concentrated by rotary evaporation and purification (Biotage Horizon HPFC system chromatography, SiO2, 20:80 EtOAc: hexane) gave the title compound as a white solid (570 mg, 30.8% yield).1H NMR (300 MHz, CDCl3, TMS): delta 7.81-7.90 (m, 2H), 7.46-7.25 (m, 8H), 6.43 (s, 1H), 5.57 (s, 1H), 4.88 (s, 1H), 1.60 (d, J=6.6 Hz, 3H).LC-MSD (ES+): m/z [310 (M+H)+, 100].

The synthetic route of 26032-72-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; US2010/144722; (2010); A1;,
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Application of 56844-12-3, 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 56844-12-3 as follows.

[0123] To diisopropylamine (1.028 ml, 7.21 mmol, 1.8 equiv) in 10 mL THF at 0 C was added n-butyl lithium (3.76 ml, 6.01 mmol, 1.5 equiv). After 1 h, the LDA solution was transferred to a solution of 6-bromo-4-chlorothieno[2,3-d]pyrimidine (1.0 g, 4.01 mmol, 1.0 equiv) in 35 mL THF at -78 C under nitrogen. The solution stirred for 1 h at -78 C after which a mixture of 1.25 mL water and 5 mL THF was added slowly. The mixture was then warmed to 0 C, poured into 60 mL water, and extracted with dichloromethane. The combined organic extracts were then dried over Na2SC> , filtered, and concentrated in vacuo to give a yellow solid which was chromatographed with 20% EtOAc/Hexanes gradient elution to give 5-bromo-4-chlorothieno[2,3-d]pyrimidine (671 mg, 67.1 % yield) as a tan solid. NMR (400 MHz, chloroform- ) delta ppm 8.85 (s, 1 H), 7.64 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56844-12-3, its application will become more common.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; MARUGAN, Juan, J.; ZHENG, Wei; SOUTHALL, Noel; HUANG, Wenwei; MCCOY, Joshua, G.; TITUS, Steven; PATNAIK, Samarjit; WO2012/44993; (2012); A1;,
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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. 62802-38-4, name is 5-Bromo-2-fluoropyrimidine, the common compound, a new synthetic route is introduced below. Product Details of 62802-38-4

To a solution of 5-bromo-2-fluoro-pyrimidine (1.0 g, 4.93 mmol) and 6,7- dihydro-5H-pyrrolo[l,2-a]imidazol-2-amine (0.87 g, 4.93 mmol) in DMSO (20 mL) was added DIEA (1.27 g, 9.86 mmol), and the mixture was stirred at 100 C for 2 h under 2 before it was allowed to cool to rt. The mixture was purified by reverse phase column chromatography (Welch Ultimate XB-C18, 40-70 muiotaeta) eluting with a gradient of 20-95% acetonitrile in water to afford N-(5-bromopyrimidin-2-yl)-6,7-dihydro-5H-pyrrolo[l,2- ]imidazol-2-amine.

The synthetic route of 62802-38-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PLEXXIKON INC.; HOLLADAY, Mark W.; LIU, Gang; (267 pag.)WO2017/19804; (2017); A2;,
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