Pyrimidines

Synthetic Route of 58004-79-8 ,Some common heterocyclic compound, 58004-79-8, molecular formula is C6H5BrN2O, 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.

Step 2. 3-Amino-6-chloro-1-ethoxycarbonyl-2-(5-pyrimidinylcarbonyl)indole The title compound was prepared according to the procedure described in step 2 of Example 1 from 4-chloro-2-(ethoxycarbonylamino)benzonitrile (Example 1, step 1) and 5-bromoacetylpyrimidine (step 1). 1H-NMR (CDCl3) delta: 9.29 (1 H, s), 9.03 (2 H, s), 8.02 (1 H, d, J=1.6 Hz), 7.57 (1 H, d, J=8.4 Hz), 7.35 (1 H, dd, J=1.6, 8.4 Hz), 6.13 (2 H, br s), 4.01 (2 H, q, J=7.1 Hz), 1.02 (3 H, t, J=7.1 Hz).

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. 58004-79-8, 2-Bromo-1-(pyrimidin-5-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; US6300363; (2001); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.1421372-67-9, name is N1-(2-(Dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)-2-nitrobenzene-1,4-diamine, molecular formula is C25H29N7O3, molecular weight is 475.5429, as common compound, the synthetic route is as follows.COA of Formula: C25H29N7O3

A 125 ml autoclave was taken, and after replacing nitrogen three times, a compound F (1.50 g, 3.15 mmol) and a Raney nickel catalyst (0.70 g) were added and dissolved in ethyl acetate (30 ml), and the hydrogen was replaced twice and then charged with 2.0 MPa of hydrogen.The temperature was raised to 40 C to stir the reaction.Filter off and wash the filter cake twice with ethyl acetate (10 ml x 2).The filtrate was concentrated under reduced pressure at 40 C to give a dark green solid: 1.36 g.The molar yield was 96.90%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1421372-67-9, N1-(2-(Dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)-2-nitrobenzene-1,4-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Zhejiang Jiuzhou Pharmaceutical Technology Co., Ltd.; Zhang Xianyi; Jiang Youyu; Wang Chong; Gao Hongjun; Che Daqing; (10 pag.)CN108129342; (2018); A;,
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Reference of 1193-21-1, 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. 1193-21-1, name is 4,6-Dichloropyrimidine. A new synthetic method of this compound is introduced below.

45.0 g (302.1 mmol) of 4,6-dichloropyrimidine are initially charged in 450 ml of water. 26.3 g (302.1 mmol) of morpholine are added, and the mixture is stirred at 90 C. for 16 h. The mixture is then cooled to 0 C., and the precipitate formed is filtered off. The precipitate is washed once with 50 ml of water and air-dried.Yield: 51.0 g (85% of theory)LC-MS (Method 4): Rt=1.09 min; MS (ESIpos): m/z=200 [M+H]+;1H-NMR (400 MHz, DMSO-d6): delta=8.35 (s, 1H), 6.95 (s, 1H), 3.62 (s, 8H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1193-21-1, 4,6-Dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Thede, Kai; Flamme, Ingo; Oehme, Felix; Ergueden, Jens-Kerim; Stoll, Friederike; Schuhmacher, Joachim; Wild, Hanno; Kolkhof, Peter; Beck, Hartmut; Akbaba, Metin; Jeske, Mario; US2012/264704; (2012); 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. 14394-70-8, name is 2-Chloro-5-methylpyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H6ClN3

[0257] A mixture of 2-cliloro-5-methylpyrimidin-4-amine (540 mg, 3.7 mmol), tot-butyl 4-(4-aminophenoxy)pirhoeridine-l-carboxylate (1.1 g, 3.7 mml) was suspended in acetic acid (20 mL) and heated at 70 C for 1 h. The mixture was allowed to cool to room temperature and acetic acid removed under reduced pressure. The residue was taken in water (20 mL) and neutralized to pH~7. The resulting solution was extracted with EtOAc (30 mL) and the organic layer separated. The organic layer was washed with brine, dried over MgStheta4 and filtered. The filtrate was concentrated in vacuo to afford the title compound (1.4 g, 95%) as a yellow solid.

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, 14394-70-8, 2-Chloro-5-methylpyrimidin-4-amine.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
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Synthetic Route of 57564-94-0, 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 57564-94-0 as follows.

To a mixture of sodium hydride (60% dispersion in mineral oil; 276 mg; 6.89 mmol) in DMF (10 mL) at 0 C was added drop-wise a solution of 4-chloro-2-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidine [prepared as detailed in Ref. 45] (1.145 g; 5.74 mmol) in anhydrous DMF (20 mL). When the addition was complete, 2-(trimethylsilyl)ethoxymethyl chloride (1.32 ml; 7.46 mmol) was added drop-wise and the reaction mixture was stirred at 0 C for 1.5 h then allowed to warm to ambient temperature. The reaction mixture was partitioned between water (100 mL) and ethyl acetate (100 mL). The organic phase was separated, dried over Na2SO4 and then filtered and the filtrate solvents evaporated in vacuo. The crude product was purified by flash chromatography on silica gel (70 g) eluting with a solvent gradient of 0-5% ethyl acetate in hexane to afford the title compound 42 (1.73 g, 91%) as a colourless oil: LC-MS (method A) tR = 2.88 min; m/z = 332, 330 [M+H]+; 1H NMR (400 MHz, DMSO-d6): delta -0.10 (s, 9H), 0.84 (t, 2H, J = 8.1 Hz), 2.53 (s, 3H), 3.52 (t, 2H, J = 8.1 Hz), 5.58 (s, 2H), 6.62 (d, 1H, J = 3.6 Hz), 7.69 (d, 1H, J = 3.6 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57564-94-0, its application will become more common.

Reference:
Article; Davies, Nicholas G.M.; Browne, Helen; Davis, Ben; Drysdale, Martin J.; Foloppe, Nicolas; Geoffrey, Stephanie; Gibbons, Ben; Hart, Terance; Hubbard, Roderick; Jensen, Michael Rugaard; Mansell, Howard; Massey, Andrew; Matassova, Natalia; Moore, Jonathan D.; Murray, James; Pratt, Robert; Ray, Stuart; Robertson, Alan; Roughley, Stephen D.; Schoepfer, Joseph; Scriven, Kirsten; Simmonite, Heather; Stokes, Stephen; Surgenor, Allan; Webb, Paul; Wood, Mike; Wright, Lisa; Brough, Paul; Bioorganic and Medicinal Chemistry; vol. 20; 22; (2012); p. 6770 – 6789;,
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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. 32779-38-7, name is 2-Chloro-5-iodopyrimidine, the common compound, a new synthetic route is introduced below. Quality Control of 2-Chloro-5-iodopyrimidine

f) 2,5-dichloro-3-(N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)sulfamoyl)benzyl acetate A mixture of 2,5-dichloro-3-(N-(3-ethynyl-2,4-difluorophenyl)sulfamoyl)benzyl acetate (1.45 g), dichlorobis(tricyclohexylphosphine)palladium(II) (246 mg), DIPEA (9 mL), copper(I) iodide (127 mg), 2-chloro-5-iodopyrimidin-2-amine (1.04 g) and DMSO (10 mL) was stirred under microwave irradiation at 60 C. for 1 hr. The same reaction was repeated twice in total, the reaction mixtures were combined, cooled to room temperature, diluted with water and ethyl acetate and an insoluble material was removed by filtration. The filtrate was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give a residue. The obtained residue was washed with ethyl acetate/IPE to give the title compound (2.60 g). 1H NMR (300 MHz, DMSO-d6) delta 2.12 (3H, s), 5.23 (2H, s), 7.21-7.31 (1H, m), 7.41 (1H, td, J=8.9, 5.9 Hz), 7.86-7.93 (2H, m), 9.03 (2H, s), 10.89 (1H, s).

The synthetic route of 32779-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); 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. 148550-51-0, name is Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C8H10N2O4S

General procedure: 60percent Sodium hydride (w/w) in mineral oil (0.0015 mol) was added to a mixture of appropriate III (0.001 mol) in THF (15 ml) under the condition of inert atmosphere using N2 flow at 5°C. The reaction mixture was kept for 1 h at room temperature. A solution of 2-(methylsulfonyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.0015 mol) in THF (15 ml) was slowly added to reaction mixture. The resulting reaction mixture was stirred for 2-3 h at 5°C. The distilled water (20 ml) was added. The reaction mixture was extracted (10 ml x 3) with dichloromethane. The separated organic layer was dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure to obtain crude product, recrytallized by ethyl acetate.

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, 148550-51-0, Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate.

Reference:
Article; Rajak, Harish; Agarawal, Avantika; Parmar, Poonam; Thakur, Bhupendra Singh; Veerasamy, Ravichandran; Sharma, Prabodh Chander; Kharya, Murli Dhar; Bioorganic and Medicinal Chemistry Letters; vol. 21; 19; (2011); p. 5735 – 5738;,
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Reference of 29274-24-6 ,Some common heterocyclic compound, 29274-24-6, molecular formula is C6H4ClN3, 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.

[0211] Step 3. Pyrazolo[1,5-alpyrimidine-5-carboxylic acid methyl ester. A mixture of 5- chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1.00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(II) dichloride (1 g, 1.42 mmol, 0.11 equiv) was stirred in a 100-mL pressure reactor overnight at 100 C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum.The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:5) to yield 1.2 g (52%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1.09 mi m/z = 178.0 [M+Hf?.

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. 29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth, W.; BAUMEISTER, Timm, R.; GOSSELIN, Francis; ZAK, Mark; ZHENG, Xiaozhang; WO2013/130935; (2013); 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. 56843-79-9, name is 4-Chloro-2-methylthieno[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 56843-79-9

General procedure: The synthesis of target compound 2-11 (Scheme 1), commenced from commercially available ethyl-2-amino-3-thiophenecarboxylate (12a, Ri= H) and ethyl-2-amino-4,5-dimethyl-3- thiophenecarboxylate obtained using a reported method. Cyclization of 12a and 12b with HC1 (g) and acetonitrile gave 13a and 13b followed by chlorination with POCl3 afforded 14a and 14b respectively. Treatment with various substituted anilines in dioxane with 2 drops of cone HC1 provided 2-11. (60 -76 % yields).

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, 56843-79-9, 4-Chloro-2-methylthieno[2,3-d]pyrimidine.

Reference:
Patent; DUQUESNE UNIVERSITY OF THE HOLY SPIRIT; GANGJEE, Aleem; (140 pag.)WO2017/31176; (2017); A1;,
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Reference of 1100318-96-4, 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. 1100318-96-4, name is 4-Iodo-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4IN3, 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.

K2CO3 was added to a solution of 4-iodo-7H-pyrrolo[2,3-d]pyrimidine (4) in dry DMF and then stirred for 30 min at room temperature. After 30 min, 2-(trimethylsilyl)ethoxymethyl chloride was added drop-wise to the solution, and the reaction was stirred for 6 h at room temperature. For quenching, saturated NH4Cl aqueous solution was added. The mixture was poured into ethyl acetate and extracted twice. The combined organic layers were dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield the desired compound.

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 1100318-96-4, 4-Iodo-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Article; Lee, Sun-Mi; Yoon, Kyoung Bin; Lee, Hyo Jeong; Kim, Jiwon; Chung, You Kyoung; Cho, Won-Jea; Mukai, Chisato; Choi, Sun; Kang, Keon Wook; Han, Sun-Young; Ko, Hyojin; Kim, Yong-Chul; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5036 – 5046;,
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