Tag: M.W:200-300

Electric Literature of 63931-21-5 ,Some common heterocyclic compound, 63931-21-5, molecular formula is C4BrCl3N2, 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.

5-Bromo-2,4,6-trichloropyrimidine (1.880 g, 6.81 mmol) was dissolved in THF (11 mL) and water (5 mL), and sodium acetate (1.68 g, 20.4 mmol), followed by 4-fluoroaniline (787 mg, 0.68 mL, 6.87 mmol) were added. The mixture was stirred at room temperature for 18 h. After that, a saturated aqueous solution of sodium hydrogencarbonate (15 mL) was added and the resulting mixture was extracted with ethyl acetate (2 x 150 mL). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 40 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 10:90) to afford, after drying in vacuo (40C, 5 mbar), the title compound as a light brown solid (2.07 g, 90%). HPLC (method LCMS_fastgradient) tR = 1.36 min. 1H NMR (CDC13, 300 MHz): delta 7.12 (dd, / = 8.3, 9.1 Hz, 2 H), 7.43 (br s, 1 H), 7.52 (dd, / = 4.6, 8.9 Hz, 2 H). MS (ES+) m/z 335.9, 337.9, 339.9 [M+H, Br & 2 CI isotopes] .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63931-21-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; JAKOB-ROETNE, Roland; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; STEINER, Sandra; (89 pag.)WO2018/11164; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 183438-24-6, 5-Bromo-2-iodopyrimidine, 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, 183438-24-6, blongs to pyrimidines compound. Recommanded Product: 183438-24-6

INTERMEDIATE 163 -(5 -Bromopyrimidin-2-yl)-3 -hydroxycyclobutyl 2,2-dimethylpropanoate5-Bromo-2-iodopyrimidine (16.7 g, 58.8 mmol) was dissolved in DCM (200 mL) with stirring and cooled to -78C under N2. n-Butyllithium in hexane (2.5M, 23.5 mL)was added dropwise and the mixture was stirred for 20 minutes at -78C. Intermediate 15 (10 g, 58.8 mmol) in DCM (50 mL) was cooled in a dry ice bath and added in one portion. The reaction mixture was stirred at -78C for 10 minutes, then quenched by the addition of saturated aqueous NH4C1 solution (20 mL) and allowed to warm to room temperature. Saturated aqueous NH4C1 solution (50 mL) was added and the mixture wasextracted with DCM (2 x 100 mL). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. The crude residue was purified by column chromatography (5i02, 0-30% EtOAc in heptane), yielding the title compound (7.6 g, 35%) as a yellow solid. H (500 MHz, CDC13) 8.78 (s, 2H), 5.22-5.14 (m, 1H), 3.03-2.93 (m, 2H), 2.67-2.58 (m, 2H), 1.22 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,183438-24-6, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; DELIGNY, Michael Louis Robert; HEER, Jag Paul; JACKSON, Victoria Elizabeth; KROEPLIEN, Boris; LECOMTE, Fabien Claude; PORTER, John Robert; WO2015/86509; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 2972-52-3, 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. 2972-52-3, name is 2,4-Dichloro-5-pyrimidinecarbonyl chloride, molecular formula is C5HCl3N2O, 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 solution of the 2,4-dichloropyrimidine-5-carbonyl chloride (24 mmol) in THF (24 ml) is added H2O (0.64 ml) at room temperature. The reaction mixture is stirred at room temperature for 0.83 h and then diluted with HaO. The mixture is extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacua to give the crude titled compound; 1H NMR (CDCI3) 5 6.80 (brs, 1H), 9.18 (s, 1H).

According to the analysis of related databases, 2972-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/18284; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 33097-11-9, 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 33097-11-9, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

4.17 6-Acetyl-7-methyl-2-(methylsulfanyl)pyrido[2,3-d]pyrimidine-4(3H)-one (13) To a stirred solution of aldehyde 1 (500 mg, 2.24 mmol) in 3.5 mL of DMF was added enamine 12 (250 mg, 2.52 mmol) followed by addition of a few drops of satd ethereal HCl. Mixture was stirred at ambient temperature for 5 h. Crystals formed were filtered, washed thoroughly with MeCN (10 mL) and dried at 110 C/5 Torr to give the titled compound (256 mg, 46%) as light pink powder, mp 265-267 C (MeCN; decomp.); numax(KBr) 3417 (br), 3008, 2731, 2625, 1726, 1716, 1690, 1627, 1524, 1426, 1371, 1345, 1263, 1227, 1163, 1108, 960, 794; deltaH (400 MHz, DMSO-d6, 60 C) 10.40 (1H, s, NH), 8.77 (1H, s, 5-H), 2.76 (3H, s, 7-CH3), 2.65 (3H, s, ?OCH3), 2.63 (3H, s, SCH3); deltaC (100.6 MHz, DMSO-d6, 60 C) 198.9 (COCH3), 165.1 (2-C), 164.0 (7-C), 161.3 (4-?), 157.3 (8a-C), 138.8 (5-C), 130.5 (6-C), 113.2 (4a-?), 29.8 (7-CH3), 24.6 (COCH3), 13.6 (SCH3); HRMS (ESI): MH+, found 250.0632. [C11H12N3O2S]+ requires 250.0645.

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 33097-11-9, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde.

Reference:
Article; Chizhova, Maria E.; Bakulina, Olga Yu.; Ivanov, Alexander Yu.; Lobanov, Pavel S.; Dar’in, Dmitrii V.; Tetrahedron; vol. 71; 36; (2015); p. 6196 – 6203;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 50593-92-5, 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. 50593-92-5, name is 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid, molecular formula is C6H5BrN2O2S, 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-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (110 g, 0.44 mol) in methanol (1.1 L) was cooled to 0C with stirreing. Thionyl chloride (50 mL, 0.66 mol) was added dropwise to the solution. The solution was slowly heated and the reaction was conducted under reflux with heating for four hours. The completion of the reaction was monitored by LC/MS and TLC and the solution was cooled to room temperature. The volatiles were distilled away under reduced pressure, and the residue was dissolved in ethyl acetate (1 L). The solution was washed with aqueous 10% sodium carbonate solution (200 mL) three times and with saturated brine (200 mL) twice. The resulting organic phase was dried over anhydrous magnesium sulfate. The solid was filtered out, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give the title compound (88 g, yield: 75%).

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 50593-92-5, 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid.

Reference:
Patent; Teijin Pharma Limited; MIZUNO, Tsuyoshi; SHIMADA, Tomohiro; UNOKI, Gen; MARUYAMA, Akinobu; SASAKI, Kosuke; YOKOSAKA, Takuya; TAKAHASHI, Hiroshi; HORIE, Kyohei; SAKAI, Yuri; (181 pag.)EP3546458; (2019); 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.866648-53-5, name is 6-Chloro-N,N-dimethyl-2-(trifluoromethyl)pyrimidin-4-amine, molecular formula is C7H7ClF3N3, molecular weight is 225.6, as common compound, the synthetic route is as follows.name: 6-Chloro-N,N-dimethyl-2-(trifluoromethyl)pyrimidin-4-amine

General procedure: 4-hydroxy was prepared in Reference Example 60 3- (piperidin-4-yl) -4- (trifluoromethyl) -1,4,5,7- tetrahydro -6H- pyrazolo [3,4-b] pyridin-6-one hydrochloride (100 mg, 0.293 mmol) in dimethyl sulfoxide (0.5 mL) solution of, N, N- diisopropylethylamine (59.8muL, 0.352mmol) and 3-chloro-6- (trifluoro methyl) pyridazine (80.2mg, 0.439mmol) was added, and the mixture was stirred overnight at room temperature.The reaction mixture was diluted with ethyl acetate, washed successively with water, saturated aqueous solution of ammonium chloride and brine, dried over anhydrous sodium sulfate, under reduced pressure, and the solvent was evaporated.The obtained residue was purified by silica gel column chromatography to obtain [eluent: ethyl acetate / methanol = 100 / 0-90 / 10 (gradient) to give the title compound (30% 39.8 mg, yield) It was.Instead of 3-chloro-6- (trifluoromethyl) pyridazine, using 6-chloro -N, N-dimethyl-2- (trifluoromethyl) pyrimidin-4-amine (150mg, 0.665mmol), carried the reaction was carried out in the same manner 80 C. manner to that described in example 43, the title compound (91 mg, yield: 28%) was obtained

At the same time, in my other blogs, there are other synthetic methods of this type of compound,866648-53-5, 6-Chloro-N,N-dimethyl-2-(trifluoromethyl)pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Daiichi Sankyo company limited; Sato, Rie; Kobayashi, Katsuhiro; Kaneko, Toshio; (188 pag.)JP2015/113323; (2015); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4359-87-9, 2,4,6-Trichloro-5-nitropyrimidine, 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, 4359-87-9, blongs to pyrimidines compound. Recommanded Product: 4359-87-9

b) 4-(2,6-Dichloro-5-nitropyrimidin-4-yl)morpholine A solution of morpholine (0.362 g, 4.2 mmol) and triethylamine (0.580 mL, 4.2 mmol) in dichloromethane (11 mL) was added dropwise to a cooled (ice-bath), stirred solution of 2,4,6-trichloro-5-nitropyrimidine (Preparation 23a, 0.950 g, 4.2 mmol) in dichloromethane (25 mL). The mixture was warmed to ambient temperature and stirred overnight. After this period the mixture was concentrated and the residue was purified by flash chromatography (3:1 hexanes/ethyl acetate) to give the title compound (0.780 g, 67%) as a yellow solid. LRMS (m/z): 279 (M+1)+. 1H NMR delta (300 MHz, CDCl3): 3.62 (m, 4H), 3.77 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4359-87-9, its application will become more common.

Reference:
Patent; Almirall, S.A.; EP2527344; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1445-39-2, Adding some certain compound to certain chemical reactions, such as: 1445-39-2, name is 2-Amino-5-iodopyrimidine,molecular formula is C4H4IN3, 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 1445-39-2.

h) 7-(N-(3-((2-aminopyrimidin-5-yl)ethynyl)-2,4-difluorophenyl) sulfamoyl)-5-chloro-2,3-dihydrobenzofuran-3-yl Acetate A mixture of 5-chloro-7-(N-(3-ethynyl-2,4-difluorophenyl)sulfamoyl)-2,3-dihydrobenzofuran-3-yl acetate (290 mg), dichlorobis(tricyclohexylphosphine)palladium(II) (50.0 mg), DIPEA (2 mL), copper(I) iodide (25.8 mg), 5-iodopyrimidin-2-amine (195 mg) and DMSO (3 mL) was stirred under microwave irradiation at 100 C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with water and 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 the title compound (254 mg). MS: [M-H]- 519.1.

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. 1445-39-2, 2-Amino-5-iodopyrimidine, other downstream synthetic routes, hurry up and to see.

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 108381-28-8, 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. 108381-28-8, name is 4-(Benzyloxy)-2-chloropyrimidine, molecular formula is C11H9ClN2O, 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.

Step 1 In a microwave vial, cis-7-methyl-8-((3,4,5-trifluorophcnyl)carbamoyl)-2,3,3a,4,10,10a-hexahydro-lH,7H-dipyrrolo[3,4-b:3′,4′-f][l,4,5]oxathiazocin-2-ium 5,5-dioxide iodide (E11) (30 mg, 0.054 mmol) and 4-(benzyloxy)-2-chloropyrimidine (24 mg, 0.109 mmol) were suspended in 1-Butanol (0.5 mL), dry DIPEA (0.030 mL, 0.172 mmol) was added and mixture was heated at l20C under MW heating for lh. UPLC-MS showed complete conversion. The mixture was evaporated under reduced pressure to afford a brown solid. The residue was purified by preparative HPLC (H20, CEbCN 0.1% TFA) to afford, after lyophilization, 2-(4-(benzyloxy)pyrimidin-2-yl)-7-methyl-N-(3,4,5-trifluorophenyl)-2,3,3a,4,l0,l0a-hexahydro-lH,7H-dipyrrolo[3,4-b:3′,4′-f][l,4,5]oxathiazocine-8-carboxamide 5,5-dioxide as a beige powder (30 mg, yield=9l%). 4-(benzyloxy)-2-chloropyrimidine was present as impurity. Product was used in next step without further purification.

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 108381-28-8, 4-(Benzyloxy)-2-chloropyrimidine.

Reference:
Patent; OSPEDALE SAN RAFFAELE S.R.L.; IRBM S.P.A.; PROMIDIS S.R.L.; ISTITUTO NAZIONALE DI GENETICA MOLECOLARE – INGM; DE FRANCESCO, Raffaele; DONNICI, Lorena; GUIDOTTI, Luca; IANNACONE, Matteo; DI FABIO, Romano; SUMMA, Vincenzo; PRANDI, Adolfo; RANDAZZO, Pietro; GORNATI, Davide; GRILLO, Alessandro; FERRANTE, Luca; BENCHEVA, Leda Ivanova; DE MATTEO, Marilenia; FERRARA, Marco; (238 pag.)WO2020/30781; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 5909-24-0, name is Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate

To 600ml of methylene dichloride was added lOOg of ethyl 4-chloro-2-(methylsulfanyl) pyrimidine-5-carboxylate and 91.2g of 3-chloro-4-methoxybenzylamine. The reaction mixture was stirred and 500m1 of water, 48g of sodium carbonate and Ig of tetra-butylammonium bromide were added to it. The reaction mixture was then maintained overnight at 25-30C. After completion of reaction, methylene dichloride layer was separated, washed with water and evaporated to obtain 145g of ethyl 4-[(3-chloro-4-methoxybenzyl) amino]-2-(methyl sulfanyl) pyrimidine-5-carboxylate having 95% of HPLC purity.

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, 5909-24-0, Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate.

Reference:
Patent; WANBURY LTD.; NITIN SHARADCHANDRA PRADHAN; VIHAR RAGHUNATH TELANGE; SURYAKANT SHIVAJI POL; SHASHIKANT BALU PADWAL; NITN SHANKAR BONDRE; WO2015/177807; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia