Tag: M.W:100-200

Synthetic Route of 1074-68-6 ,Some common heterocyclic compound, 1074-68-6, molecular formula is C6H6N2OS, 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.

Preparation of 3-hydroxy-3-(2-methylsulfanyl-pyrimidin-4-yl)-propionic acid tert-butyl ester (18): To a cold (0 C.) solution of diisopropylamine (5.7 mL, 40.5 mmol) in THF (130 mL) is added dropwise n-butyllithium (16.2 mL of a 2.5 M solution in hexanes, 40.5 mmol). The mixture is stirred for 45 min at 0 C., then the solution is cooled to -78 C. tert-Butyl acetate (5.5 mL, 40.5 mmol) is added dropwise to the reaction mixture. After stirring 40 min at -78 C., a solution of 2-methylsulfanyl-pyrimidine-4-carbaldehyde (5.0 g, 32.4 mmol) is added dropwise. After 30 min at -78 C., the solution is poured into aqueous saturated NH4Cl. The aqueous phase is extracted with EtOAc. The organic phase is dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified over silica (5% EtOAc/hexanes, followed by 20% EtOAc/hexanes) to afford 7.2 g (82% yield) of the desired product. 1H NMR (300 MHz, CDCl3) delta 8.52 (d, J=5.1 Hz, 1H), 7.22 (d, J=5.1 Hz, 1H), 5.00 (dd, J=8.4, 3.6 Hz, 1H), 2.93 (dd, J=16.5, 3.6 Hz, 1H), 2.70 (dd, J=16.5, 7.8 Hz, 1H), 2.58 (s, 3H), 1.46 (s, 9H); ESI+ MS: m/z (rel intensity) 271.1 (85, M++H).

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. 1074-68-6, 2-Methylsulfanylpyrimidine-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Procter & Gamble Company; US2005/113392; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 34415-10-6, name is 2-Methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 2-Methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid

A mixture of 6-hydroxy-2-methylpyrimidine-4-carboxylic acid (500 mg) and phosphorus oxychloride (5 mL) was heated under reflux under a nitrogen atmosphere for 2 hr. The solvent was evaporated under reduced pressure. To the residue was added THF (3 mL). The reaction mixture was added dropwise to a mixture of 1-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)phenyl)methanamine (732 mg), TEA (646 mg) and dichloromethane (8 mL) at 0C over 10 min, and the reaction mixture was stirred at the same temperature for 2 hr. The reaction mixture was diluted with water, and the aqueous layer was extracted with dichloromethane. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (198 mg) . MS: [M+H]+ 360.1.

The synthetic route of 34415-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; HIRAYAMA, Takaharu; HIRATA, Yasuhiro; TOMINARI, Yusuke; IWAMURA, Naoki; SASAKI, Yusuke; ASANO, Moriteru; TAKAGI, Terufumi; OKANIWA,Masanori; YOSHIDA, Masato; ICHIKAWA, Takashi; IMAMURA, Shinichi; (113 pag.)EP3514149; (2019); A1;,
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Related Products of 5267-07-2, 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 5267-07-2, name is 5-Pyrimidineacetic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-bromobenzene-l ,2-diamine (10) (0.281g, 1.5mmol) , 2-(pyrimidin-5-yl)acetic acid (11) (0.207g, 1.5mmol), and HATU (0.741g, 1.95mmol) in DCM (50ml) was added triethylamine (0.63ml, 4.5mmol). The reaction mixture was stirred at room temperature overnight. The solution was washed with saturated sodium bicarbonate (50ml) and brine (50ml). The DCM solution was dried over sodium sulfate and concentrated. The residue was purified by automated column chromatography columned using DCM and methanol as eluents. Yield 0.4g, 87%. MS: m/z 306.9 (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 5267-07-2, 5-Pyrimidineacetic acid.

Reference:
Patent; ZALICUS PHARMACEUTICALS LTD.; PAJOUHESH, Hassan; HOLLAND, Richard; ZHANG, Lingyun; PAJOUHESH, Hossein; LAMONTAGNE, Jason; WHELAN, Brendan; WO2012/116440; (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. 57401-76-0, name is Ethyl 2-aminopyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 57401-76-0

To a solution of ethyl 2-aminopyrimidine-5-carboxylate (0.200 g, 1.196 mmol) in DME (6 ml), a suspension of sodium 2-methylbutan-2-olate (0.527 g, 4.79 mmol) in DME (6 ml) was added drop wise stirring at room temperature under nitrogen. The resulting yellow suspension was stirred at the same temperature for 30 minutes and then cooled to -10C. Methanesulfonyl chloride (0.278 ml, 3.59 mmol) was added drop wise maintaining the temperature below – 5C. After 1.5 hours water (30 ml) was added and the mixture was extracted with ethyl acetate (20 ml x 3). The combined organic layers were dried over sodium sulfate and evaporated. The residue was triturated with MeOH and the mother liquors were evaporated and triturated with EtOH. The two portions collected by filtration were mixed affording 0.152 g of a mixture of ethyl 2-(methylsulfonamido)pyrimidine-5-carboxylate and methyl 2-(methylsulfonamido)pyrimidine-5-carboxylate (about 1 : 1 ratio). This mixture was suspended in THF (6.380 ml) and 3N NaOH (0.425 ml, 1.276 mmol) was added. The resulting solution was heated to 50C for 2.5 hours. THF was evaporated and the aqueous solution was diluted with water (2 ml) and acidified with 6N HC1 (pH = 2) stirring at room temperature. The obtained precipitate was collected by filtration affording 2-(methylsulfonamido)pyrimidine-5-carboxylic acid as a white solid (0.133 g, 0.612 mmol, 51.1% yield, MS/ESI+ 218.0 [MH] +).

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, 57401-76-0, Ethyl 2-aminopyrimidine-5-carboxylate.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ARMANI, Elisabetta; AMARI, Gabriele; CAPALDI, Carmelida; ESPOSITO, Oriana; PERETTO, Ilaria; WO2013/45280; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1801-06-5 ,Some common heterocyclic compound, 1801-06-5, molecular formula is C5H4ClFN2O, 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 AA1 : 5-(r(2S.5f?)-4-ethyl-2.5-dimethylpiperazin-1-vncarbonyl)-lambda/-(5-fluoro-2- methoxypyrimidin-4-yl)-6,6-dimethyl-1 ,4,5.6-tetrahvdropyrrolof3.4-clpyrazol-3-amine; A solution of 5-{[(2S,5f?)-4-ethyl-2,5-dimethylpiperazin-1-yl]carbonyl}-6,6-dimethyl- 1 ,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-amine (289 mg, 0.9 mmol) and 4-chloro-5- fluoro-2-methoxypyrimidine (257 mg, 2 eq) in 5 ml_ of 50percent acetic acid in water was heated in a microwave for 30 min at 8O0C. Purification as described in Example AJ. afforded the title compound AA1 as a white powder (13.1 mg, 3percent). See Table 1 below for NMR data.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1801-06-5, its application will become more common.

Reference:
Patent; PFIZER INC.; WO2008/96260; (2008); A1;,
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Pyrimidine – Wikipedia

Application of 42839-08-7, Adding some certain compound to certain chemical reactions, such as: 42839-08-7, name is Ethyl pyrimidine-2-carboxylate,molecular formula is C7H8N2O2, 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 42839-08-7.

General procedure: To the solution of ester (10 mmol) in THF (20 mL) and ethyl acetate (70 mmol), LiHMDS (30 mmol) was added very quickly at -40 C, and stirred at this temperature for 20 min. After completion of the reaction, reaction mixture was quenched with acetic acid (50 mmol) and then basified using 10% NaHCO3 solution, extracted with ethyl acetate (2×100 mL), the combined organic layer was washed with water and brine solution and dried over Na2SO4. The specific purification procedure for each compound has been included along with their characterization data.

According to the analysis of related databases, 42839-08-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Venkat Ragavan; Vijayakumar; Rajesh; Palakshi Reddy; Karthikeyan; Suchetha Kumari; Bioorganic and Medicinal Chemistry Letters; vol. 22; 12; (2012); p. 4193 – 4197;,
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Reference of 186519-92-6, Adding some certain compound to certain chemical reactions, such as: 186519-92-6, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid,molecular formula is C7H4ClN3O2, 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 186519-92-6.

To a stirred suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (G-l) (3.11 g,15.7 mmol, 1.0 eq) and a catalytic amount of DMF in a mixture of DCM (40 mL) and THF (40 mL) at RT, oxalyl dichloride (2.0 mL, 23.5 mmol, 1.5 eq) is added dropwise. The resulting mixture is stirred for 2 h and then concentrated in vacuo. The residue (G2) is dissolved in DCM (50 mL) and the resulting solution is added dropwise to saturated aqueous ammonium hydroxide (200 mL) at RT. The resulting mixture is stirred for 30 min and then filtered. The filter cake is then rinsed with H20 (30 mL X 2). The filtrate is acidified with con. HC1 to adjust the pH to 4-5. The solid is collected by filtration, rinsed with water and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine- 5-carboxamide (G-3).

According to the analysis of related databases, 186519-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTELLIKINE, INC.; INFINITY PHARMACEUTICALS, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; CASTRO, Alfredo, C.; EVANS, Catherine, A.; WO2011/146882; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 216309-28-3 , The common heterocyclic compound, 216309-28-3, name is 5-((Trimethylsilyl)ethynyl)pyrimidine, molecular formula is C9H12N2Si, 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.

(8S,9S)-9-epi-Azido-9-dehydroxy quinine (1.045 g, 3.0 mmol)was dissolved in a mixture of tert-butanol and water (12 mL, 1:1,v/v), and 2-(TMS-ethynyl)-pyrimidine (631 mg, 3.58 mmol,1.2 equiv) was added. Then pyridine (0.25 mL, 3.1 mmol,1.0 equiv), CuSO4.5H2O (290 mg, 1.25 mmol 0.4 equiv), sodiumascorbate (494 mg, 2.49 mmol, 0.8 equiv) and K2CO3 (806 mg,5.83 mmol, 1.9 equiv) were added. The suspension was stirred atroom temperature for 3 days. Then saturated aqueous Na2S solutionwas added and the mixture stirred for an additional 0.5 h,while dark brown precipitate formed. The mixture was filteredthrough Celite and washed with CH2Cl2. The filtrate was washedwith water, dried over Na2SO4 and evaporated. Chromatographyon silica gel (CHCl3/MeOH, 10:1 v/v.) gave white crystalline solid(1.233 g, 91%). M.p.: 248.53-250.7 C, [a]D21 = -182 (c 0.91, CH2Cl2).1H NMR (600 MHz, CDCl3) delta 8.81 (d, J = 4.4 Hz, 1H), 8.69 (d,J = 4.7 Hz, 2H), 8.15 (s, 1H), 7.99 (d, J = 9.1 Hz, 1H), 7.603-7.57(m, 1H), 7.50 (d, J = 4.7 Hz, 1H), 7.34 (dd, J = 9.1, 2.2 Hz, 1H), 7.11(t, J = 4.9 Hz, 1H), 6.51 (d, J = 11.3 Hz, 1H), 5.91 (ddd, J = 17.5,10.7, 6.9 Hz, 1H), 5.08 (d, J = 9.4 Hz, 1H), 5.06 (d, J = 18.2 Hz, 1H),3.94 (s, 3H), 3.933-3.88 (m, 1H), 3.493-3.42 (m, 1H), 3.14 (dd,J = 14.0, 10.1 Hz, 1H), 2.74 (dd, J = 14.3, 4.1 Hz, 1H), 2.713-2.65(m, 1H), 2.343-2.27 (m, 1H), 1.96 (t, J = 11.9 Hz, 1H), 1.793-1.76(m, 1H), 1.653-1.54 (m, 2H), 0.94 (dd, J = 14.1, 7.1 Hz, 1H)(Fig. S8a, SI).13C NMR (151 MHz, CDCl3) delta 159.1, 158.8, 157.4, 147.3, 147.2,145.1, 141.4, 138.8, 132.0, 128.2, 123.4, 122.6, 119.5, 119.2,114.8, 100.8, 61.0, 58.0, 56.1, 55.9, 41.1, 39.1, 27.74, 27.72, 27.70(Fig. S8a, SI).HRMS (ESI) Calc. for [C26H27N7O+H]+: 454.2350, found:454.2353 (Fig. S5, SI).

The synthetic route of 216309-28-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ga??zowska; Boraty?ski; Kowalczyk; Lipke; Czapor-Irzabek; Polyhedron; vol. 121; (2017); p. 1 – 8;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 38275-43-3, 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. 38275-43-3, name is 2-(Methylthio)pyrimidine-5-carbonitrile, molecular formula is C6H5N3S, 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.

To a mixture of 2-(methylsulfanyl)pyrimidine-5-carbonitrile (25.00 g, 165.35 mmol, 1.00 eq) and hydroxylamine hydrochloride (22.98 g, 330.70 mmol, 2.00 eq) in ethanol (250.00 ml) and water (250.00 ml) was added sodium hydrogen carbonate (27.78 g, 330.70 mmol, 2.00 eq). The reaction was stirred at 70 C for 16 h. This mixture was filtered and washed with water (50 ml*4). The residue was collected and evaporated. This residue N’-hydroxy-2-(methylsulfanyl)pyrimidine-5- carboximidamide (29.00 g, crude) was used for next step without further purification

According to the analysis of related databases, 38275-43-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; BRUNET, Stephane; GOeRTZ, Andreas; GOURGUES, Mathieu; HILT, Emmanuelle; JAKOBI, Harald; NAUD, Sebastien; REBSTOCK, Anne-Sophie; DUCERF, Sophie; (78 pag.)WO2019/122323; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 69205-79-4, 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 69205-79-4 as follows.

Anew synthesis of 7-formyl-preQ0 (systematic name, 2-amino-5-formylpyrrolo[2,3-d]pyrimidin-4-one) that, contrary to literature-known procedures (21-23), does not require protecting group chemistry was developed. PreQ0 (808 mg, 4.61 mmol)and sodium hypophosphite dihydrate (1.44 g, 13.6 mmol) were dissolved in the solvent mixture (15 ml of pyridine/acetic acid/deionized water in a ratio of 2:1:1) and stirred under inert atmosphere.Raney nickel catalyst (slurry in water, 500 mg) wasadded to the stirred reaction mixture. Safety precaution: dryRaney nickel is pyrophoric and should always be handled underinert atmosphere. The resulting reaction mixture was heated to50 C for 5 h. Subsequently, the reaction mixture was cooled to room temperature and filtered over a pad of celite. The filtrate was reduced in vacuo. The remaining brown residue was dissolvedin 6 M aqueous potassium hydroxide solution. The remaining solids were filtered off. The filtrate was cooled to 0 Cand neutralized by addition of concentrated aqueous HCl. Theproduct precipitated from the solution and was isolated by filtrationand washed with copious amounts of ice water and acetone(brown solid, 770 mg, 94%). 1H NMR (DMSO-d6) 6.35(bs, 2H, NH2), 7.49 (s, 1H, H-8), 10.04 (s, 1H, CHO), 10.72 (bs,1H, H-9), 11.96 (bs, 1H, H-1); 13C NMR (DMSO-d6) 98.36(C-7), 120.34 (C-8), 124.50 (C-5), 153.40 (C-2), 153.83 (C-4),159.02 (C-6), 185.47 (CHO). NMR data were recorded on aBruker AVANCE III with autosampler (1H NMR 300.36 MHz,13C NMR 75.53 MHz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69205-79-4, its application will become more common.

Reference:
Article; Jung, Jihye; Czabany, Tibor; Wilding, Birgit; Klempier, Norbert; Nidetzky, Bernd; Journal of Biological Chemistry; vol. 291; 49; (2016); p. 25411 – 25426;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia