Tag: M.W:100-200

Synthetic Route of 287714-35-6 ,Some common heterocyclic compound, 287714-35-6, molecular formula is C6H5ClN2O2, 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.

2-Chloropyrimidine-5-carboxylic acid methyl ester (434mg, 2.33 mmol) was added to a stirring suspension of (2R)-2-amino-3-methyl-3-{[(2E)-3,7,11,15- tetramethylhexadec-2-en-1-yljsulfanyl}butanoic acid (ig, 2.33 mmol) and N,Ndiisopropylethylamine (1.2lmL, 6.99 mmol) in dioxane (lOmL) at room temperature and heated to 60C overnight. The reaction mixture is cooled to room temperature and washed once with brine. The reaction mixture is diluted with an additional 5mL of dioxane, followed by addition of 1M lithium hydroxide (lOmL) at room temperature and stirred overnight. The reaction mixture is diluted with ethyl acetate, washed with 10% w/v citric acid solution, then brine and dried over magnesium sulfate. The ethyl acetate is filtered and concentrated on a rotary evaporator to give the crude product as a yellow oil that is purified by flash chromatography using ethyl acetate in hexanes as the eluent to give the purified carboxylic acid as an off-white solid. The carboxylic acid was dissolved in ethanol, then solid sodium ethoxide was added until the pH reached 9. The resulting ethanolic suspension was centrifuged at 2000 rpm for 2 minutes. The ethanol was decanted and the ethanol wash was repeated twice more. Acetonitrile was then substituted for ethanol and the wash was repeated three times. The resulting solid was dried on a rotary evaporator to give 165mg of a white solid in 12% yield. ?H NMR (500 MHz, Deuterium Oxide) 8.61 (s, 2H), 5.07 (s, 1H), 4.21 (s, 1H), 3.17 – 3.02 (m, 2H), 1.92 – 1.74 (m, 2H), 1.49 (d, J = 6.4 Hz, 3H), 1.44 – 0.82 (m, 26H), 0.79 – 0.64 (m, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,287714-35-6, its application will become more common.

Reference:
Patent; SIGNUM BIOSCIENCES, INC.; VORONKOV, Michael; PEREZ, Edwardo; HEALY, Jason; FERNANDEZ, Jose; (139 pag.)WO2018/132759; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 14080-59-2, Adding some certain compound to certain chemical reactions, such as: 14080-59-2, name is 4-Chlorothieno[2,3-d]pyrimidine,molecular formula is C6H3ClN2S, 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 14080-59-2.

4-Chlorothieno[2,3-d]pyrimidine (10) (5.80 g, 34.0 mmol) was dissolved in dry THF (300 mL) under nitrogen, cooled to -78 C, n-butyllithium (1.1 equiv, 23.4 ml, 1.6 M in hexane) was added and the mixture stirred at -78 C for 4 h. An excess of solid carbon dioxide was added and the mixture allowed to warm up to room temperature overnight. The solvents were removed under reduced pressure, and the remaining solid was suspended in water (300 mL). The suspension was filtered over a pad of celite and the clear solution was acidified with conc. HCl under stirring. The precipitating colourless crystals were collected by filtration and dried. 65% yield; colourless crystals; mp 195 C (decomp.); 1H NMR (300 MHz, DMSO-d6): delta 9.01 (s, 1H), 8.07 (s, 1H) ppm. MS (ESI+): 256 ([MH++CH3CN]+, 100; 35Cl), 215 ([M+H]+, 12; 35Cl). IR (KBr): nu 3442, 3091, 1724 cm-1. Anal. (C7H3ClN2O2S; 214.63): C, H, N.

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. 14080-59-2, 4-Chlorothieno[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Beckers, Thomas; Sellmer, Andreas; Eichhorn, Emerich; Pongratz, Herwig; Schaechtele, Christoph; Totzke, Frank; Kelter, Gerhard; Krumbach, Rebekka; Fiebig, Heinz-Herbert; Boehmer, Frank-D.; Mahboobi, Siavosh; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 125 – 136;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 14161-09-2, Adding some certain compound to certain chemical reactions, such as: 14161-09-2, name is 2-(Methylsulfonyl)pyrimidine,molecular formula is C5H6N2O2S, 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 14161-09-2.

Example 124 3-(pyrimidin-2-yloxy)-5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazole Compound A (0.100 g, 0.34 mmol) and B (0.268 g, 1.69 mmol) were added to a 0.2-5 mL microwave tube. DMF (3 mL) was added. The mixture was stirred and microwaved at 120 C. for 30 min, and then filtered. The filtrate was purified by HPLC. The fractions from HPLC were combined, K2CO3 (0.5 g) were added, extracted with EtOAc. The organic solution was concentrated. The resultant material was filtered through a short silica gel column with 1% MeOH in EtOAc to afford the title compound (6.4 mg, 5%). 1H NMR (400 MHz, DMSO-d6) delta 8.74 (d, J=4.8 Hz, 2H), 8.03 (dd, J=9.0, 1.8 Hz, 1H), 7.95-7.88 (m, 2H), 7.83-7.75 (m, 2H), 7.45 (t, J=4.8 Hz, 1H), 7.44-7.39 (m, 2H). m/z: 374 (MH+)

According to the analysis of related databases, 14161-09-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Graupe, Michael; Lu, Yafan; Zablocki, Jeff A.; US2015/175560; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1722-12-9, 2-Chloropyrimidine, 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, 1722-12-9, blongs to pyrimidines compound. name: 2-Chloropyrimidine

Example 7 N-(1-Methyl-5-phenyl-1H-imidazol-2-yl)-3-phenyl-propionamide (90) To a solution of 2-chloropyrimidine (90a, 2.0 g, 17.5 mmol) in THF (25 mL) was added 40% CH3NH2(aq) (7.5 mL) at 0 C. The reaction mixture was stirred at 50 C. for 1.0 hour and then poured into saturated NaHCO3(aq) and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure to give N-methylpyrimidin-2-amine (90b).To a microwave vial containing a solution of N-methylpyrimidin-2-amine (90b, 290 mg, 2.7 mmol) in acetonitrile (5 mL) was added 2-bromo-1-phenylethanone (714 mg, 3.6 mmol). The vial was sealed and heated in a microwave reactor at 130 C. for 20 minutes and then cooled to room temperature. The reaction mixture was treated with hydrazine hydrate (0.65 mL, 13.3 mmol) and then heated in a microwave reactor at 100 C. for 5.0 minutes. The solution was poured into water and filtered the precipitate to give 1-methyl-5-phenyl-1H-imidazol-2-ylamine (90c).To a solution of 1-methyl-5-phenyl-1H-imidazol-2-amine (90c, 52.0 mg, 0.3 mmol) in pyridine (1.0 ml) was added 3-phenyl-propionyl chloride (60.7 mg, 0.36 mmol). The reaction mixture was stirred at room temperature for 16 hours, quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give N-(1-Methyl-5-phenyl-1H-imidazol-2-yl)-3-phenyl-propionamide (90) : 1H NMR (500 MHz, DMSO) delta: 7.16-7.48 (m, 10H), 6.87 (s, 1H), 3.42 (s, 3H), 3.07 (t, 2H), 2.92 (t, 2H). ESI-MS: 305.7 (M+H)+.Compounds 91 was synthesized in a manner similar to that describe above and its observed ESI-MS was 309.8 (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,1722-12-9, its application will become more common.

Reference:
Patent; DEVELOPMENT CENTER FOR BIOTECHNOLOGY; US2012/172374; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 39906-04-2, Adding some certain compound to certain chemical reactions, such as: 39906-04-2, name is 4,6-Dichloro-2-methylpyrimidin-5-amine,molecular formula is C5H5Cl2N3, 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 39906-04-2.

General procedure: A microwave vial was charged with the corresponding aniline (1 , 1 .0 mmol), the 4,6-dichloropyrimidine (2, 1 .0 mmol), isobutanol (2.5 mL) and 37% aqueous HCI (0.07 mL/mmol). The reaction vessel was sealed and heated in a microwave reactor at 150 C for 10-30 min. After cooling, the reaction mixture was worked up as indicated in each case. Following the general procedure, a microwave vial was charged with 5-amino- 4,6-dichloro-2-methylpyrimidine (200 mg, 0.48 mmol), 3-chloroaniline (50 muIota_, 0.48 mmol), isobutanol (1 .2 mL) and 37% aqueous HCI (36 muIota_). After cooling, the product was isolated by filtration and dried to obtain 120 mg (93%) of 3c as a brown solid. Mp: 239-241 C. MS (ES, positive mode): m/z 269 (M+H)+with a 2 CI isotopic pattern. 1 H NMR (DMSO-d6, 300 MHz): delta 2.33 (s, 3H, CH3), 6.38 (s, 2H, NH2), 7.05 (ddd, J = 8.0, 2.0, 0.8 Hz, 1 H, H-4′), 7.33 (pt, J = 8.1 Hz, 1 H, H-5′), 7.73 (ddd, J = 8.3, 2.0, 0.8 Hz, 1 H, H-6′), 7.99 (pt, J = 2.1 Hz, 1 H, H-2′), 9.1 1 (s, 1 H, NH).

According to the analysis of related databases, 39906-04-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; CONSEJO SUPERIOR DE INVESTIGACIONS CIENTIFICAS (CSIC); PEREZ PEREZ, Maria Jesus; GIGANTE MARTINEZ, Alba; CANELA GOMEZ, Maria Dolores; LEYSSEN, Pieter; NEYTS, Johan; WO2014/170368; (2014); 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. 1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine. A new synthetic method of this compound is introduced below., Safety of 2-Methyl-4,6-dichloropyrimidine

At room temperature,1.50 kg of 2-amino-N-(2-chloro-6-methylphenyl)-5-thiazolamide,1.11kg of 4,6-dichloro-2-methylpyrimidine was added to a 50L reactor.Add 13.35kg of tetrahydrofuran,Nitrogen protection, stirring and cooling to -5 C ~ 10 C,The temperature of the reaction solution is maintained at -5C to 10C, and sodium tert-butoxide solids are added to the reaction solution in several portions.The total amount of tert-butoxide sodium solids is 2.13kg, and the addition method is to feed once every 20-30min.Each time no more than 10% of the total and no more than 200g,After the addition, the reaction liquid is allowed to react at -5C to 10C for 1 to 2 hours.After warming the reaction solution to 10 C ~ 30 C,Stir the reaction solution,To HPLC detection of 2-amino-N-(2-chloro-6-methylphenyl)-5-thiazoleamide/N-(2-chloro-6-methylphenyl)-2-[(6-chloro- The amount of 2-methyl-4-pyrimidinyl)amino]-5-thiazolecarboxamide is less than 1.5%.Cool the reaction solution to -10C to 10C.Dropping hydrochloric acid at a concentration of 4 mol/L,Adjust the system pH to 6 to 7,After dropping, continue stirring at -10C10C for 12h,filter,The filter cake is washed with an appropriate amount of water and methanol.The filter cake is vacuum dried at 50-60C.N-(2-chloro-6-methylphenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5-thiazolecarboxamide 1.364kg, yield 74.06%;

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, 1780-26-3, 2-Methyl-4,6-dichloropyrimidine.

Reference:
Patent; Huarun Shuang He Limin Pharmaceutical (Jinan) Co., Ltd.; Qin Yunpeng; Jiang Yang; Gao Hongxu; (12 pag.)CN107089976; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3001-72-7, 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 3001-72-7, name is 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The p-nitrophenyl carbonate derivative (0.3 g) was dissolved in AR grade THF (5 mL) at room temperature and DBU or DBN (2 equiv) was added. The temperature of the reaction mixture was raised to 60 C and stirring was continued for 1 h. After completion, the reaction mixture was extracted with ethyl acetate (2 × 30 mL), the organic layer washed with saturated NaHCO3 solution, water, brine and dried over anhydrous Na2SO4. Thesolvent was evaporated and the crude compound was purified by column chromatography

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 3001-72-7, 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine.

Reference:
Article; Vangala, Madhuri; Shinde, Ganesh P.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2086 – 2092;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 42754-96-1, 4,6-Dichloro-1H-pyrazolo[3,4-d]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, 42754-96-1, blongs to pyrimidines compound. Recommanded Product: 42754-96-1

4-(6-chloro-lH-pyrazolo[3,4-d]pyrimidin-4-ylamino)-benzenesulfonamide 4A was prepared from IA and IB in dioxane at RT in 10% yield. MS 325 (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,42754-96-1, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/39359; (2008); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3001-72-7, 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 3001-72-7 as follows.

General procedure: A mixture of dimethyl 3-amino-4-cyano-9H-fluorene-1,2-dicarboxylate (1 mmol), carbon disulfide (3 mmol) andDBU or DBN (1 mmol) in DMF (1.5 mL) was stirred for12 h in room temperature. After completion of the reaction(confirmed by TLC), the solvent was removed underreduced pressure. The residue was washed with water (5 ml)and recrystallized from EtOH to afford the pure product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3001-72-7, its application will become more common.

Reference:
Article; Ahadi, Somayeh; Zolghadr, Mahdi; Shakibaei, Ghazaleh Imani; Bazgir, Ayoob; Journal of the Iranian Chemical Society; vol. 13; 2; (2016); p. 369 – 375;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 2227-98-7, 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. 2227-98-7, name is 4-Aminopyrrolo[3,2-d]pyrimidine. A new synthetic method of this compound is introduced below.

Example 18.4: (+/-)-c/s-1-[(9-Deaza-adenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine (34); Formaldehyde (35 muL, 0.4 mmol, 37 wt% solution in water) followed by 9-deazaadenine (52 mg, 0.4 mmol) are added to a solution of 33 (32 mg, 0.3 mmol) in 1 ,4-dioxane (1 ml.) and water (1 ml_). The reaction mixture is stirred at room temperature for 68 h, absorbed onto silica and eluted down a silica column using a gradient 10 – 50% (7 N NH3 in MeOH) in CH2CI2. The crude product is collected, concentrated and subjected to flash chromatography (5 : 4.9 : 0.1 then 5 : 4.8 : 0.2, CH2CI2 : MeOH : 28% aq. NH4OH) to afford 34 as an off-white solid (45 mg, 62%). 1H NMR (500 MHz, CD3OD): delta = 8.16 (s, 1H), 7.49 (s, 1H), 4.20 (td, J = 5.8, 3.3 Hz, 1H), 3.89 (s, 2H), 3.17 (dd, J = 10.9, 5.5 Hz, 1 H), 2.95 (dd, J = 9.4, 7.5 Hz, 1H), 2.57 (dd, J = 10.9, 3.3 Hz, 1 H), 2.41 (t, J = 9.9 Hz, 1H), 2.00 – 1.92 (m, 1H), 1.61 – 1.53 (m, 1H), 1.38 – 1.28 (m, 1 H) and 0.92 ppm (t, J = 7.5 Hz, 3H). 13C NMR (125 MHz, CD3OD): delta = 152.1 , 151.0, 147.0, 130.1 , 115.1 , 112.7, 72.5, 63.0, 58.3, 49.4, 46.6, 21.4 and 13.2 ppm. ESI-HRMS for C13H20N5O [MH]+ calcd, 262.1668; found, 262.1663.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2227-98-7, 4-Aminopyrrolo[3,2-d]pyrimidine, and friends who are interested can also refer to it.

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia