Tag: M.W:100-200

Synthetic Route of 4994-86-9 ,Some common heterocyclic compound, 4994-86-9, molecular formula is C5H5ClN2, 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.

In a microwave tube 4-chloro-2-methylpyrimidine (50 mg, 0.3 89 mmol), 6- bromo-3-fluoro-2-methylpyridine (73.9 mg, 0.389 mmol), 1,1,1,2,2,2- hexamethyldistannane (127 mg, 0.389 mmol) and Pd(Ph3P)4 (22.47 mg, 0.019 mmol)were taken in DMF (4 mL). The reaction mixture was purged with nitrogen and heated at 160 C under microwave for 1 h. The reaction mixture was concentrated, diluted with brine and ethyl acetate. The organic layer was separated, dried over Na2SO4, filtered, and concentrated which afforded brownish oil. The crude product was purified by silica gel chromatography (20-40% ethyl acetate-hexane) to afford 4-(5-fluoro-6-methylpyridin-2-yl)-2-methylpyrimidine (72 mg, 0.354 mmol, 91% yield). LCMS (ESI) m/e 204.5 [(M+H), calcd for C11H11FN3 204.11; LC/MS retention time (method B): tR = 0.75 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4994-86-9, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4595-59-9, 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 4595-59-9 as follows.

EXAMPLE 22A 5-Pyrimidin-5-yl-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic Acid Tert-Butyl Ester A mixture of the product of Example 6C (2.045 g, 9.63 mmol), 5-bromopyrimidine (1.84 g, 11.6 mmol), tris(dibenzylideneacetone)dipalladium (0) Pd2(dba)3, Strem, 0.265 g, 0.29 mmol), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, Strem, 0.30 g, 0.48 mmol) and tert-BuONa (sodium tert-butoxide, 1.85 g, 19.3 mmol) in 75 mL PhCH3 was degassed three times with a N2 back-flush. The mixture was warmed to 85 C., stirred for 48 h then was cooled, filtered and concentrated under reduced pressure. Purification by column chromatography (SiO2, 50% hexanes-EtOAc) gave 2.68 g of the title compound (9.23 mmol, 95% yield). MS (DCI/NH3) m/z 291 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-59-9, its application will become more common.

Reference:
Patent; Basha, Anwer; Bunnelle, William H.; Dart, Michael J.; Gallagher, Megan E.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Ryther, Keith B.; Tietje, Karin R.; US2005/65178; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]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, Application In Synthesis of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

LDA (2 M in cyclohexane/ethylbenzene/THF; 32.04 mL, 64.09 mmol) was added dropwise to a stirred solution of intermediate 115 (19 g, 61.03 mmol) in THF (244 mL) at -78 C to -60 C under nitrogen atmosphere. The mixture was stirred at -60 C for 40 minutes. Then 7-chloro-5-methyl-[l,2,4]triazolo[l,5-a]pyrimidine (CAS: 24415-66-5; 10.29 g, 61.03 mmol) dissolved in the minimum amount of THF was added dropwise and the mixture was stirred at -60 C to -70 C for 1 h. The mixture was quenched with NH4CI (aq. sat. soltn.) and concentrated in vacuo. The residue was partitioned between EtOAc and water. The layers were separated and the aqueous layer was extracted with EtOAc (x 2). The combined organic layers were dried (MgS04), filtered and concentrated in vacuo yielding intermediate 116 (27 g, 99.7% yield) used as such in the subsequent reaction step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres Avelino; ALCAZAR-VACA, Manuel Jesus; (192 pag.)WO2018/154133; (2018); 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. 34289-60-6, name is 4,6-Dimethylpyrimidin-2-ol hydrochloride, the common compound, a new synthetic route is introduced below. Recommanded Product: 34289-60-6

General procedure: An equimolar mixture (0.0125 mol) of 2-hydroxypyrimidines 1-2 and a corresponding arylcarboxaldehyde in 80 ml of ethanol was stirred for about 15min and then treated with 2.5 mL of HCl (cc). The obtained reaction mixture was heated under reflux for 6 h togive the corresponding hydrochlorides as red solids, which were then neutralized by 10% aqueous-alcoholic solution of carbonate of potassium. The resulting products (yellow solids) were filtered off, washed by hotethanol and dried in the air.

The synthetic route of 34289-60-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Komissarova, Ekaterina A.; Sosnin, Evgenii; Shklyaeva, Elena V.; Osorgin, Irina V.; Abashev, Georgii G.; Arkivoc; vol. 2017; 3; (2017); p. 105 – 120;,
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Pyrimidine – Wikipedia

Reference 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.

Example 4b: Preparation of acetyl-N-(2.6-dichloropyrimidin-4-yl)hvdroxylamine (DCAP-Ac)2,6-Dichloropyrimidin-4-amine (DCAP, 20 g, 121.95 mmol) was suspended in acetic anhydride (400 mL, 4.27 mol, 35 molEq), and the suspension was heated to reflux. The obtained solution was stirred at reflux for 3.5 hours. The resulting reaction mixture was then cooled, concentrated to dryness in vacuo and the remaining acetic anhydride was removed by evaporation with toluene portions. The residue was dissolved in ethyl acetate (333 mL) and water (333 mL) and pH was adjusted to 7 by addition of 10% NaHC03. The organic layer was washed with saturated NaCl solution, and then evaporated to dryness. The residue was dissolved in acetic anhydride (cca 200 mL) and stirred at 0-5 C for 2 h. The precipitate that formed was filtered off and dried 5h / 40 C / 10 mbar.Yield: 18.34 (68%) of acetyl-N-(2,6-dichloropyrimidin-4-yl)hydroxylamine (DCAP-Ac). Purity (HPLC): 100 area %.

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 10132-07-7, 4-Amino-2,6-dichloropyrimidine.

Reference:
Patent; ASSIA CHEMICAL INDUSTRIEW LTD.; TEVA PHARMACEUTICALS USA, INC.; ?EPELJ MAJER, Maja; KRIZMANIC, Irena; ?EPAC, Dragan; WO2012/170647; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 105806-13-1, 4,6-Dichloro-5-fluoro-2-methylpyrimidine, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

Part A: 4-Chloro-6-[(2R)-2,4-dimethyl-1-piperazinyl]-5-fluoro-2-methylpyrimidine. To a solution of (3R)-1 ,3-dimethylpiperazine dihydrochloride (Example 63) (5.88 g, 31.4 mmol) in dichloromethane (126 mL) was added N,N-diisopropylethylamine (18.1 1 mL, 104 mmol), and 4,6-dichloro-5-fluoro-2-methylpyrimidine (5.69 g, 31.4 mmol). The solution was heated at 35 0C and stirred for 3 days. The solution was cooled to room temperature, diluted with DCM (100 mL), and washed with sat. aq. NaHCOs (100 mL). The aqueous phase was extracted with a fresh portion of DCM (50 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give crude 4-chloro-6-[(2R)-2,4-dimethyl-1-piperazinyl]-5-fluoro-2- methylpyrimidine (9.60 g, >100 % yield) as a brown oil that was used without further purification. LCMS: (M+H)+: 258.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105806-13-1, 4,6-Dichloro-5-fluoro-2-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/61879; (2009); A1;,
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.1208170-17-5, name is 4-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile, molecular formula is C7H6ClN3S, molecular weight is 199.66, as common compound, the synthetic route is as follows.name: 4-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile

General procedure: A mixture of 3a,b (2.86 mmol), 4-methoxyaniline (0.36 g,2.88 mmol) and anhydrous K2CO3 (0.4 g, 5.76 mmol) inEtOH (15 ml) was heated under reflux for 5 h. It was thencooled, filtered and the filtrate was concentrated to half itsvolume. The obtained precipitate was filtered and crystallizedfrom EtOH-H2O (3:1 v/v).4-(4-Methoxyanilino)-6-methyl-2-(methylthio)-pyrimidine-5-carbonitrile (4a) Yield 71%; mp 158-160 C; IR v/cm-1:3300 (NH), 2214 (C?N), 1614 (C=N), 1604 (C=C-Ar),1293, 1134 (vas and vs C-O-C); 1H NMR (CDCl3, 60 MHz)delta/ppm: 7.49 (d, 2H, Ar-Hs, o- to NH-Ar, J = 12.6 Hz), 7.21(s, br, 1H, NH), 6.90 (d, 2H, Ar-Hs, o- to OCH3, J = 12.0Hz), 3.83 (s, 3H, OCH3), 2.58 (s, 3H, S-CH3), 2.50 (s, 3H,CH3); EIMS m/z 286 (M+., 100), 271 (33), 270 (25), 238(13); Anal. Calcd. for C14H14N4OS: (286.35): C, 58.72; H,4.93; N, 19.72. Found: C, 58.97; H, 4.98; N, 19.57.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1208170-17-5, 4-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Farghaly, Ahmed M.; AboulWafa, Omaima M.; Elshaier, Yaseen A. M.; Badawi, Waleed A.; Haridy, Haridy H.; Mubarak, Heba A. E.; Medicinal Chemistry Research; vol. 28; 3; (2019); p. 360 – 379;,
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Pyrimidine – Wikipedia

Related Products of 18592-13-7, 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 18592-13-7, name is 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

6-Chloromethyl uracil (500 mg, 3.1 mmol) was dissolved in THF (50 mL) and the solution was treated with 4-methoxybenzyl alcohol (860 mg, 6.2 mmol), triphenylphosphine (2.45 g, 9.3 mmol) and diisopropylazodicarboxylate (1.26 g, 6.2 mmol). The reaction was allowed to stir overnight at room temperature. The mixture was then poured over water (75 mL) and was extracted with ethyl acetate (3*50 mL). The combined organic extracts were dried over Na2SO4, filtered and reduced. Compound 28a was isolated and purified by normal phase column chromatograpy (silica gel, 20% EtOAc/heptane-100% EtOAc/heptane). M+ (ES+)=401.1.

According to the analysis of related databases, 18592-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Coats, Steven J.; Dyatkin, Alexey B.; He, Wei; Lisko, Joseph; Miskowski, Tamara; Ralbovsky, Janet L.; Schulz, Mark; US2008/269225; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 55583-59-0, 2,5-Diamino-4,6-dichloropyrimidine, 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, Formula: C4H4Cl2N4, blongs to pyrimidines compound. Formula: C4H4Cl2N4

In a reaction vessel, 4,6-dichloropyrimidine-2,5-diamine (1.00 g, 5.59 mmol),4- (N, N-Dimethylamino) phenylboronic acid(0.922 g, 5.5 9 mmol),Sodium carbonate (2.96 g, 27.9 mmol),To a solution of tetrakis (triphenylphosphine) palladium (0) (0.323 g, 0.560 mmol) in toluene (56 mL) was added ethanol (14 mL) and distilled water (14 mL) at room temperature, and then under an argon atmosphere. After stirring for 20 hours under heating and reflux conditions, the reaction solution was cooled to room temperature. Distilled water (16 mL) was added and stirred, and the separated aqueous layer was extracted three times with ethyl acetate (20 mL).Thereafter, the whole organic layer was combined, saturated aqueous sodium chloride solution (20 mL) was added thereto, the mixture was stirred and washed, anhydrous sodium sulfate was added to the separated organic layer for dehydration, and the filtrate after filtration was concentrated under reduced pressure .The concentrate thus obtained is purified by flash column chromatography (silica gel, n-hexane / ethyl acetate),4-Chloro-6- (4- (dimethylamino) phenyl) pyrimidine-2,5-diamine(0.727 g, 49% yield).

The synthetic route of 55583-59-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Microbial Chemistry Research Foundation; Kumagai, Naoya; Noda, Hidetoshi; Asada, Yasuko; Shibazaki, Masakatsu; (48 pag.)JP2019/64981; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
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Application of 5466-43-3 ,Some common heterocyclic compound, 5466-43-3, molecular formula is C7H6Cl2N2, 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.

Morpholine (0.32 mL, 3.7 mmol) was added to a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (0.5 g, 2.65 mmol) in anhydrous ethanol (5 mL) and stirred at a temperature in the range of 65 C. to 85 C. for 10 to 16 hours. Thereafter, the mixture was concentrated under reduced pressure and the crude was diluted with anhydrous ether. After standing at a temperature in the range of 5 C. to 10 C. for 2 hours, the precipitated solid was filtered and washed with ether. The solid was recrystallized from ethyl acetate to afford the title compound as a pale yellow solid (0.54 g, 86% yield).1H NMR (CDCl3, 300 MHz): delta 4.10-3.94 (m, 4H), 3.90-3.76 (m, 4H), 3.36-3.20 (m, 2H), 3.10-2.90 (m, 2H), 2.29-2.12 (m, 2H).LC-MSD (ES+): (m/z) 240 [(M+H)+, 100].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5466-43-3, its application will become more common.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; US2010/144731; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia