Tag: M.W:100-200

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. 155-12-4, name is 2-Chloro-5-fluoropyrimidin-4-one, molecular formula is C4H2ClFN2O, 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. Computed Properties of C4H2ClFN2O

Example 1b 2-(2-Chloro-5-fluoro-6-oxo-6H-pyrimidin-1-ylmethyl)-benzonitrile The title compound was prepared in 44% yield from 2-chloro-5-fluoro-3H-pyrimidin-4-one as described in U.S. patent application Ser. No. 10/918,317. Specifically, 5-Fluoro-2-chloro-3H-pyrimidin-4-one was stirred in DME/DMF under nitrogen at 0 C. Sodium hydride (95%) was added in portions. After 10 min, lithium bromide was added and the reaction stirred at r.t. alpha-Bromo-o-tolunitrile was added, and the reaction stirred at 65 C. for 8 h. The solution was diluted with EtOAc, washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by silica gel chromatography (1:1:1 EtOAc/hexanes/CHCl3) gave the title compound. Also obtained from the reaction were impure fractions of the less polar O-alkylated isomer, and the more polar N3-alkylated isomer. 1H NMR (400 MHz, CDCl3): delta 7.81 (s, 1H), 7.74 (dd, 1H, J=7.6, 1.2 Hz), 7.59 (td, 1H, J=7.6, 1.2 Hz), 7.45 (t, 1H, J=7.6 Hz), 7.15 (d, 1H, J=7.6 Hz), 5.67 (s, 2H). MS (ES) [m+H] calc’d for C12H7N3OFCl, 264, 266; found 264, 266.

With the rapid development of chemical substances, we look forward to future research findings about 155-12-4.

Reference:
Patent; Chyall, Leonard J.; Lorimer, Keith; McClausland, Linda J.; US2007/66636; (2007); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 2227-98-7, 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 2227-98-7, name is 4-Aminopyrrolo[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 17.4: (3f?,4S)-4-Butyl-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxypyrrolidine (20, R = Et); Formaldehyde (86 mul_, 1.1 mmol, 37 wt% solution in water) followed by 9-deazaadenine (112 mg, 0.84 mmol) are added to a solution of 19 (R = Et) (100 mg, 0.56 mmol) in 1 ,4-dioxane (1 mL) and water (2 ml_). The reaction mixture is warmed to 85 0C and after 1 h the crude reaction mixture absorbed onto silica and eluted down a silica column using a gradient 5 – 30% (7 N NH3 in MeOH) in CH2CI2. The crude product is collected, concentrated and subjected to flash chromatography (5 : 4.5 : 0.5, CH2CI2 : MeOH : 28% aq. NH4OH) to afford 20 (R = Et) as an off- white solid (90 mg, 56%). 1H NMR (500 MHz, CD3OD): delta = 8.17 (s, 1H), 7.49 (s, 1H), 3.86 – 3.83 (m, 1 H), 3.81 (q, J = 13.2 Hz, 2H), 3.05 (dd, J = 9.6, 8.0 Hz, 1H), 2.74 (dd, J = 10.4, 6.3 Hz, 1 H), 2.69 (dd, J = 10.4, 4.0 Hz, 1H), 2.17 (dd, J = 9.7, 8.0 Hz. 1H), 1.98 – 1.90 (m, 1H), 1.57 – 1.47 (m, 1H), 1.34 – 1.24 (m, 5H) and 0.89 ppm (t, J = 6.9 Hz, 3H). 13C NMR (125 MHz, CD3OD): delta = 152.1 , 151.0, 147.0, 130.1 , 115.1, 112.6, 77.8, 62.4, 59.7, 49.1 , 48.6, 34.0, 31.5, 23.8 and 14.4 ppm. ESI-HRMS for C15H24N5O [MH]+ calcd, 290.1981; found, 290.1988

According to the analysis of related databases, 2227-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBERT EINSTEIN COLLEGE OF YESHIVA UNIVERSITY; INDUSTRIAL RESEARCH LIMITED; EVANS, Gary Brian; LONGSHAW, Alistair Ian; SCHRAMM, Vern L.; TYLER, Peter, Charles; WO2011/8110; (2011); A1;,
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Reference 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.

General procedure: The respective halomethyl derivatives {6-(chloromethyl)uracil (0.1150g, 0.716mmol) or 4-bromomethyl-7-methoxycoumarin (0.1928g, 0.716mmol)} were suspended in acetone (1.5cm3) and then added individually to alkaline mixtures comprised of NaOH (0.0286g, 0.716mmol) in distilled water (1cm3). Upon dissolution of the organic precursors, the corresponding solutions were introduce in a dropwise manner to particular reaction mixtures of di(2-picolyl)amine (0.1001g, 0.5024mmol) and K2CO3 (0.069g, 0.5018mmol) in acetone (4.0cm3). Thereafter, the resultant reaction mixtures were heated at reflux for 24h, which was followed by the reduction of the solvent under vacuum. The respective residues were dispersed in separate 1:1 (v:v) water and chloroform combinations. Then the crude individual oily products were attained by the triplicate extractions from the aqueous mixture using chloroform and these extracts were dried over anhydrous MgSO4 prior to removing the solvent under reduced pressure. The relating crude products were purified by column chromatography using a silica stationary phase and DCM: MeOH (v:v, 9:1) as a mobile phase. 2.2.2 6-((bis(pyridin-2-ylmethyl)amino)methyl)uracil (Hurdpa) X-ray quality single crystals were grown via the slow diffusion of n-hexane into a solution of dichloromethane. Yield: 0.72g (51%). Molecular mass (m/z): Cald. for C17H17N5O2: 323.14. Found: 346.13 [M+Na]+ (Fig. S3). FTIR (cm-1): v(N-H) 3370 (br, w); v(C=O) 1681 (vs); v(C=N) 1579 (s); v(C-N) 1161, 1136 (m). 1H NMR (d6-DMSO/ppm/298K, Fig. S4): 11.04 (br, s, 1H, N5H); 10.87 (s, 1H, N4H); 8.55-8.50 (m, 2H, H1, H12); 7.84-7.75 (m, 2H, H3, H10); 7.52-7.46 (m, 2H, H2, H11); 7.33-7.24 (m, 2H, H4, H9); 5.57 (s, 1H, H17); 3.90-3.83 (m, 4H, H6, H6?, H7, H7?); 3.52 (br, s, 2H, H13, H13?). UV-Vis (MeOH, lambdamax (epsilon, M-1cm-1)): 256nm (sh, 1540); 262nm (1720); 268nm (sh, 1350); 359nm (10)

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 18592-13-7, 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione.

Reference:
Article; Gramni, Larusha; Vukea, Nyeleti; Chakraborty, Abir; Samson, William John; Dingle, Laura Margaret Kirkpartick; Xulu, Bheki; de la Mare, Jo-Anne; Edkins, Adrienne Lesley; Booysen, Irvin Noel; Inorganica Chimica Acta; vol. 492; (2019); p. 98 – 107;,
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Pyrimidine – Wikipedia

Related Products of 7461-50-9, 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 7461-50-9, name is 2-Chloropyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-(5-aminopyrazin-2-yl)-6-cyclobutyl-2-fluorophenol (17.0 g, 65.6 mmol), K2CO3 (13.6 g, 98.4 mmol), 2-chloropyrimidin-4-amine (8.9 g, 69 mmol), 18-crown-6 (0.87 g, 3.3 mmol), and DMA (131 mL) was stirred at 120 Celsius for 15 hours. Water (306 mL) was added, and the reaction mixture cooled to room temperature. Solid precipitate was collected by vacuum filtration and dried in a vacuum oven at 70 Celsius to give the crude product (23.1 g, 100%). The solid was recrystallized from EtOH and treated successively with activated charcoal and silica-supported thiol to remove residual Pd and afford the title compound (13.0 g, 56%). MS (ESI): mass calcd. for C18H17FN6O, 352.14; m/z found, 353.2 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 8.25 (s, 1H), 8.01 (d, J=1.5, 1H), 7.83 (d, J=5.8, 1H), 7.66 (m 1H), 7.23 (d, J=8.3, 1H), 7.06 (s, 2H), 6.67 (s, 2H), 6.17 (d, J=5.8, 1H), 3.60-3.47 (m, 1H), 2.19-2.01 (m, 4H), 1.98-1.85 (m, 1H), 1.80-1.68 (m, 1H).

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 7461-50-9, 2-Chloropyrimidin-4-amine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2015/252008; (2015); A1;,
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Pyrimidine – Wikipedia

Related Products of 16357-69-0, 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.16357-69-0, name is 4-Aminopyrimidine-5-carbonitrile, molecular formula is C5H4N4, molecular weight is 120.11, as common compound, the synthetic route is as follows.

General procedure: Substrate (1.0 mmol), [HDBN+][TFE-] (6.0 mmol) were loaded in a 10 mL glass reaction tube equipped with a magnetic stirrer. The air in the reactor was replaced by CO2. Then, the reactor was stirred at the desired temperature for 3-96 h under CO2 using a balloon. After the reaction, the reaction liquid was cooled to room temperature and quenched by saturated ammonium chloride solution. Then the mixture was filtered to afford the crude product, which was purified by chromatography (silica gel, methanol/dichloromethane=1/20) to give the desired compound. The purified product was characterized by NMR and HR-MS. 1H NMR and 13C NMR studies were carried out with a JEOL NMR 400 (400 MHz, 100 MHz) spectrometer with DMSO-d6 as the solvent. Mass spectra were recorded with an AMD40223(Interambulacra) spectrometer.

The chemical industry reduces the impact on the environment during synthesis 16357-69-0, I believe this compound will play a more active role in future production and life.

Reference:
Article; Li, Chun; Lu, Xunhua; Yang, Yuanyong; Yang, Shenggang; Zhang, Lin; Tetrahedron Letters; vol. 59; 25; (2018); p. 2463 – 2466;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 10320-42-0, 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. 10320-42-0, name is 2-Chloro-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

(3S)-1o-(3-aminopyrrolidin- 1-yl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H- [1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid (40 mg, 0.115 mmol, 1 eq) was dissolved in dimethyl sulfoxide (2 mL) with 2-Chloro-5-nitropyflmidine (36.74 mg, 0.230 mmol, 2 eq) in a s mL capacity microwave vessel fitted with a magnetic stirrerbar and microwaved at 160¡ãC for 1.5 hours. The DMSO was evaporated the compound was crystalized using hot ethanol to afford compound A1.27. 1H NMR (400 MHz, DMSO-d6) 6 15.38 (br. s., 1H), 9.15 (d, J = 3.30 Hz, 1H), 9.08 (d, J= 3.30 Hz, 1H), 8.90 (s, 1H), 7.56 (d, J = 14.12 Hz, 1H), 4.90-4.85 (m, 1H), 4.60 – 4.56 (m, 1H), 4.53 (d, J = 11.74 Hz, 1H), 4.28 (d, J = 11.19 Hz, 1H), 4.05 ? 3.90 (m, 2H), 3.75 – 3.83-3.68 (m, 2H), 2.22 (tcl, J = 6.53, 12.79 Hz, 1H), 2.05 (dcl, J = 6.51, 12.56 Hz, 1H),1.45 (ci, J = 6.79 Hz, 3H); Formula C21H19FN606 LC-MC Retention time 3.362 mm,Found 471.1 [M+H]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10320-42-0, 2-Chloro-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; KING’S COLLEGE LONDON; THE SECRETARY OF STATE FOR HEALTH; RAHMAN, Khondaker Mirazur; JAMSHIDI, Shirin; LAWS, Mark Benjamin; NAHAR, Kazi; SUTTON, John Mark; HIND, Charlotte; (265 pag.)WO2018/220365; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 73576-33-7, 4-Chloro-6-isopropylpyrimidin-2-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, 73576-33-7, blongs to pyrimidines compound. Quality Control of 4-Chloro-6-isopropylpyrimidin-2-amine

General procedure: 2-Amino-4-chloro-6-isopropylpyrimidine (3, 1.0 mmol,171.6 mg) or 143.6 mg 2-amino-4-chloro-6-methylpyrimidine(4, 1 mmol), 62.8 mg iodoferrocene (1, 0.2 mmol),3.4 mg Pd(OAc)2 (0.01 mmol), 5.4 mg PPh3 (0.02 mmol),146 mm3 triethylamine (1.0 mmol), and 4 cm3 DMF weretransferred under an inert atmosphere into a stainless steelautoclave. It was charged with carbon monoxide (30 bar atroom temperature) and stirred at 100 C for 3 h. Theproducts were isolated by column chromatography (silica,eluent: n-hexane/EtOAc = 1/1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73576-33-7, its application will become more common.

Reference:
Article; Fehr, Csaba; Habu, Ivan; Wouters, Johan; Skoda-Foeldes, Rita; Monatshefte fur Chemie; vol. 145; 12; (2014); p. 1981 – 1986;,
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Pyrimidine – Wikipedia

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. 22536-61-4, name is 2-Chloro-5-methylpyrimidine. A new synthetic method of this compound is introduced below., Safety of 2-Chloro-5-methylpyrimidine

(E)-2-(but-2-en-2-yl)-5-methylpyrimidine, Example 10.01. 2- Chloro-5-methyl-pyrimidine (18 mL, 151 mmol), potassium (Z)-but-2-en-2- yltrifluoroborate (Sigma Aldrich, 31 g, 191 mmol), tricyclohexylphosphine (8.5 g, 30.2 mmol), and Pd2(dba)3 (13.82 g, 15.09 mmol) were added to a flask, which was then degassed and backfilled with nitrogen. To the flask was added 1,4-dioxane (252 mL) and aqueous potassium phosphate tribasic (37.5 mL, 453 mmol). The resulting reaction was heated at 100 C for 16 h. The reaction was then cooled to RT. The residue was filtered through a plug of silica gel, then loaded onto silica gel (0-20% EtOAc in heptanes) to afford (E)-2-(but-2-en-2-yl)-5-methylpyrimidine 10.01 (19 g, 125 mmol, 83% yield).

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, 22536-61-4, 2-Chloro-5-methylpyrimidine.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 14080-23-0 ,Some common heterocyclic compound, 14080-23-0, molecular formula is C5H3N3, 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.

Pyrimidine-2-carboxylic acid (11):To a stirred solution of pyrimidine-2-carbonitrile (10) (201 mg, 1.914 mmol) in water (5 mL), KOH (214.3 mg, 3.83 mmol) was added and the reaction was refluxed for 3 h. After consumption of the starting material (by TLC), the reaction was slowly brought to RT, neutralized with 2N HC1 and water was removed from the reaction mixture to give the crude residue which was extracted with EtOAc. The combined organic extracts were filtered through a pad of celite and the filtrate was concentrated under reduced pressure to provide compound 11 (84 mg, 35.4%) which was carried for the next step without any purification.TLC: 80% EtOAc/Hexane (Rf: 0.05)1H NMR (400MHz, CD3OD-d4): delta 8.83 (br s, 2H), 7.47 (t, J = 4.8 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14080-23-0, its application will become more common.

Reference:
Patent; THERACRINE, INC.; SUN, Lijun; BARSOUM, James; WESTER, Ronald; WO2013/13238; (2013); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 7431-45-0, Adding some certain compound to certain chemical reactions, such as: 7431-45-0, name is 2-Phenylpyrimidine,molecular formula is C10H8N2, 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 7431-45-0.

General procedure: In a Schlenk tube, a solution of R3In (0.375 mmol, ~0.3M en THF) and the arylpyridine (0.25 mmol)were successively added to a solution of Rh(PPh3)3Cl (24 mg, 0.025 mmol) in chlorobenzene (20 mL).The mixture was stirred at 120 C during 48 h, and the reaction quenched by addition of dropsof MeOH. The solvent was evaporated and CHCl3 (25 mL) was added. The organic phase waswashed with aq. NH3 (5%, 15 mL), dried, filtered, and concentrated. The crude was purified by flash chromatography (Et2O/hexane) affording, after concentration and drying, the cross-coupling products.

According to the analysis of related databases, 7431-45-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Riveiros, Ricardo; Tato, Ruben; Sestelo, Jose Perez; Sarandeses, Luis A; Molecules; vol. 23; 7; (2018);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia