Pyrimidines

Synthetic Route of 5750-76-5, 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. 5750-76-5, name is 2,4,5-Trichloropyrimidine. A new synthetic method of this compound is introduced below.

General procedure: A solution of 2,4,5-trichloropyrimidine(1.82 g, 10 mmol), (2-aminophenyl)dimethylphosphine oxide(1.69 g, 10 mmol) and N,N-diisopropylethylamine (1.94 g, 15 mmol)in propan-2-ol (25 mL) was heated under reflux for 12 h. The solvent was removed by evaporation and the residue was dissolvedin CH2Cl2 (100 mL). The solution was washed with water andsaturated sodium chloride solution and dried, filtered andconcentrated. The residuewas purified by flash chromatography onsilica gel (0e2% MeOH in DCM) to afford compound 51l (1.60 g,50%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5750-76-5, 2,4,5-Trichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Chen, Yongfei; Wu, Jiaxin; Wang, Aoli; Qi, Ziping; Jiang, Taoshan; Chen, Cheng; Zou, Fengming; Hu, Chen; Wang, Wei; Wu, Hong; Hu, Zhenquan; Wang, Wenchao; Wang, Beilei; Wang, Li; Ren, Tao; Zhang, Shanchun; Liu, Qingsong; Liu, Jing; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 674 – 697;,
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Application of 7033-39-8 ,Some common heterocyclic compound, 7033-39-8, molecular formula is C6H7BrN2O2, 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.

General procedure: To a mixture of 1,3-dimethyluracil (0.140 g, 1 mmol), CuBr (0.057 g, 0.4 mmol, 0.4 equiv), and the aryl iodide (2 mmol, 2 equiv) in DMF (2 mL) was added LiOtBu (0.320 g, 4 mmol, 4 equiv). The reaction mixture was heated at reflux temperature for 1 h. After cooling to the room temperature, the reaction was quenched by adding saturated aqueous NH4Cl solution.The solvent was removed under reduced pressure. The residue was partitioned between EtOAc and H2O. The organic layer was washed with saturated aqueous NaCl solution, dried over anhydrous MgSO4, and then concentrated under reduced pressure to dryness. The residue was purified by flash column chromatography to give the product.

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. 7033-39-8, 5-Bromo-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cheng, Chien; Shih, Yu-Chiao; Chen, Hui-Ting; Chien, Tun-Cheng; Tetrahedron; vol. 69; 4; (2013); p. 1387 – 1396;,
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Reference of 10457-14-4 ,Some common heterocyclic compound, 10457-14-4, molecular formula is C10H20N2O2Si2, 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.

Compound 8c (703 mg, 1.24 mmol), bis-TMS uracil (630 mg, 2.46 mmol), and silver(I)triflate (630 mg, 2.46 mmol) were placed into a microwave vial under argon, and anhydrous dichloroethane (5 mL) and acetonitrile (5 mL) were added. The mixture was heated at 135 C. for 30 minutes via use of a microwave reactor. The reaction mixture was cooled to room temperature, filtered, and the volatiles were removed in vacuo. The crude material was purified via chromatography on silica gel (eluent: hexanes/EtOAc) affording Compound 8d (504 mg, 0.845 mmol) as a single isomer. 1H-NMR (400 MHz, CDCl3): delta 8.08 (d, J=7.2 Hz, 2H), 8.03-8.00 (m, 4H), 7.62-7.37 (m, 10H), 6.36 (d, J=5.6 Hz, 1H), 6.11 (m, 1H), 5.66 (dq, J=7.2/2.8 Hz, 1H), 4.50 (dd, J=8.4/2.4 Hz, 1H), 4.90 (m, 1H), 1.57 (d, J=6.8 Hz, 3H) ppm. MS=596 (M+H+). LC/MS retention time on a 6 minute LC/MS method (Polar RP column)=4.43 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10457-14-4, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; US2012/263678; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 271-70-5, 7H-Pyrrolo[2,3-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, 271-70-5, blongs to pyrimidines compound. category: pyrimidines

General procedure: Procedure C: A solution of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine (1, 0.4 g, 3.0 mmol), 5-bromo-2-(4-methoxybenzyl) isoindolin-1-one (2, 1.0 g, 4.5 mmol) and potassium phosphate (1.91 g, 9.0 mmol) in 1, 4-dioxane (15 ml) was degassed with nitrogen for 10 min. Copper (I) iodide (0.28 g, 1.5 mmol) and trans-1, 2-diaminocyclohexane (0.17 g, 1.5 mmol) were added and the reaction was refluxed at 90 C. for 16 h. Progress of the reaction was monitored by TLC. After completion, solvent was removed under reduced pressure. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The organic layer was separated, dried over sodium sulphate, filtered and concentrated under reduced pressure to afford 2-(4-methoxybenzyl)-5-(4-methyl-7H-pyrrolo [2, 3-d] pyrimidin-7-yl) isoindolin-1-one (3) as a yellow solid. Yield: 0.55 g, 47%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,271-70-5, its application will become more common.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 74901-69-2, 2,4-Dichloro-6,7-dihydrothieno[3,2-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, 74901-69-2, blongs to pyrimidines compound. Quality Control of 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine

To a solution of 2,4-dichloro-6,7-dihydrothieno[3,2-d]pyrimidine (2.50 g, 12 mmol) in DMSO (8 mL) was added DIPEA (4.2 mL, 24 mmol) and 6-oxaspiro[3.3]heptan-2- amine hydrochloride (2.00 g, 13 mmol) was added. The reaction mixture was stirred at rt overnight. Water ( 10 mL) was added and the obtained slurry was stirred for 30 min before filtration and subsequent washings with water afforded the title compound as solid material. 1H NMR (DMSO-d6) delta: 7.43 (d, J = 7.1 Hz, 1H), 4.62 (s, 2H), 4.49 (s, 2H), 4.26 (h, J = 8.1 Hz, 1H), 3.39 – 3.31 (m, 2H), 3.17 – 3.08 (m, 2H), 2.62 – 2.53 (m, 2H), 2.30 – 2.16 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74901-69-2, its application will become more common.

Reference:
Patent; LEO PHARMA A/S; LARSEN, Jens; (110 pag.)WO2019/57806; (2019); A1;,
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Application of 151266-23-8 , The common heterocyclic compound, 151266-23-8, name is 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine, molecular formula is C5H4IN5, 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.

To a suspension of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (103) (2.0 g, 7.66 mmol) in anhydrous N,N-dimethylformamide (50 mL) under an argon atmosphere, potassium carbonate (4.23 g, 30.6 mmol) and bromocyclopentane (1.37 g, 9.20 mmol, 1.2 eq) were added sequentially. The resulting mixture was stirred at 80 C. for 5 h and then was allowed to cool to room temperature. The mixture was filtered and the filtrate was concentrated to half volume in vacuo and then partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford the desired product, 1-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (601) (1.27 g, 50.4% yield) as a yellow solid. ESI-MS (M+H)+ m/z: 330.1.

The synthetic route of 151266-23-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Intellikine LLC; Ren, Pingda; Liu, Yi; Wilson, Troy Edward; Li, Liansheng; Chan, Katrina; US2015/225407; (2015); A1;,
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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.5018-38-2, name is 4,6-Dichloro-5-methoxypyrimidine, molecular formula is C5H4Cl2N2O, molecular weight is 179, as common compound, the synthetic route is as follows.Recommanded Product: 5018-38-2

P16 10 To a solution of 4-fluorophbetanol (630 mg, 5.61 mmol) in 20 ml THF at rt was added 1BuOK (815 mg, 7.26 mmol, 1.3 eq.) and mixture for about 10 min. and cooled to 0 0C. To this was added 4,6-dichloro-5-methoxypyrimidine (1.0 g, 5.59 mmol) in one portion and the mixture was stirred overnight while allowing to warm to rt. It was quenched with aq. NH4CI, extracted 3x with ethyl acetate, the combined organic layer was washed with brine, dried over MgSO4, filtered, concentrated and the residue purified by flash chromatography using 10% ethyl acetate in hexanes to provide 950 mg of P16 and 14 mg of 10.LCMS for 10: 331.2 (MH+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5018-38-2, 4,6-Dichloro-5-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; CHELLIAH, Mariappan, V.; CHACKALAMANNIL, Samuel; GREENLEE, William, J.; EAGEN, Keith, A.; GUO, Zhuyan; CLASBY, Martin, C.; XIA, Yan; JAYNE, Charles, L.; DWYER, Michael; KEERTIKAR, Kartik, M.; CHAN, Tin-Yau; WANG, Li; WO2011/17296; (2011); A1;,
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Related Products of 42754-96-1, Adding some certain compound to certain chemical reactions, such as: 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine,molecular formula is C5H2Cl2N4, 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.

Example 14.6-Chloro-N-(pyridin-4-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine A mixture of 4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine (83 mg, 0.439 mmol), 4- (aminomethyl)pyridine (67 mg, 0.619 mmol) and DIPEA (0.30 mL, 1.72 mmol) in 1,4- dioxane (2.0 mL) was heated in a sealed tube at 100 C for 45 min, then cooled to room temperature. The solvents were removed by rotary evaporation, and the crude residue was purified by chromatography on silica gel (gradient 0-100% CMA in dichloromethane). The product isolated from chromatography was dissolved in acetonitrile/water, frozen and lyophilized to afford the title compound (43.8 mg, 38%) as an off-white solid: ESI MS [M+H]+ m/z 261; 1H NMR (300 MHz, DMSO-d6) G 13.63 (br s, 1H), 9.25 (t, J = 6.3 Hz, 1H), 8.53 (d, J = 5.9 Hz, 2H), 8.17 (s, 1H), 7.35 (d, J = 5.8 Hz, 2H), 4.73 (d, J = 5.7 Hz, 2H).

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. 42754-96-1, 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; UNITED STATES DEPARTMENT OF HEALTH AND HUMAN SERVICES; SLAUGENHAUPT, Susan, A.; JOHNSON, Graham; PAQUETTE, William, D.; ZHANG, Wei; MARUGAN, Juan; (306 pag.)WO2016/115434; (2016); A1;,
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Electric Literature of 5177-27-5 ,Some common heterocyclic compound, 5177-27-5, molecular formula is C4H3Cl2N3, 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.

1-t-Butoxycarbonyl-piperazine (2.36 g) was condensed with 2,4-dichloro-pyrimidin-5- ylamine (2.0 g) in dimethylsulfoxide (20 ml) in the presence of triethylamine (5.3 ml) according to the method described in Example 1, Step A. 4-(5-Amino-2-chloro-pyrimidin-4- yl)-piperazine-1-carboxylic acid tert-butyl ester (3.4 g) was obtained as violet crystals. MS (ES+) 314/316 (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,5177-27-5, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2005/115146; (2005); A1;,
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Application of 397308-78-0, 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.397308-78-0, name is 4-Hydroxy-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H6N2O3S, molecular weight is 186.19, as common compound, the synthetic route is as follows.

In a 250mL round bottom flask with magnetic stir bar, 4-hydroxy-2- (methylsulfanyl)pyrimidine-5-carboxylic acid (12 g, 64.45 mmol, 1.00 eq.) was suspended in thionyl chloride (120 mL). The resulting solution was stirred for 18 h at 80 C, and then concentrated under reduced pressure to afford the acid chloride intermediate.

The chemical industry reduces the impact on the environment during synthesis 397308-78-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK PATENT GMBH; QIU, Hui; CALDWELL, Richard D.; NEAGU, Constantin; MOCHALKIN, Igor; LIU-BUJALSKI, Lesley; JONES, Reinaldo; TATE, Devon; JOHNSON, Theresa L.; GARDBERG, Anna; WO2015/61247; (2015); A2;,
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