Tag: M.W:200-300

Reference of 514854-13-8, 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.514854-13-8, name is 6-Ethyl-5-iodopyrimidine-2,4-diamine, molecular formula is C6H9IN4, molecular weight is 264.07, as common compound, the synthetic route is as follows.

According to a general Sonogahisra coupling procedure, ethyl-iodopyrimidine (0.105 g, 0.4 mmol), CuI (0.028 g, 0.08 mmol, 21 mol %), Pd(PPh3)2Cl2 (0.028 g, 0.04 mmol, 10 mol %) and alkyne 45 (0.123 g, 0.6 mmol) were reacted in DMF/Et3N (1.3 mL each) at 60 C. for 12 h. After the mixture was cooled, dark reddish brown solution was concentrated and the product was purified by flash chromatography (SiO2, 5 g, 2% MeOH/CHCl3) to afford coupled pyrimidine 48 as a pale white powder (0.099 g, 71%) followed by reverse phase flash chromatography (NH2 capped SiO2, 3 g, 100% CH2Cl2, 1% MeOH/CH2Cl2) for biological evaluation: TLC Rf=0.1 (5% MeOH/CH2Cl2); mp 161.3-162.8 C.; 1H NMR (500 MHz, CDCl3) delta 8.84 (s, 2H), 8.62-8.02 (m, 2H), 7.88-7.37 (m, 3H), 5.16 (s, 2H), 4.98 (s, 2H), 4.10 (q, J=7.1 Hz, 1H), 2.67 (q, J=7.6 Hz, 2H), 1.65 (d, J=7.2 Hz, 3H), 1.22 (t, J=7.6 Hz, 3H); 13C NMR (12 MHz, CDCl3) delta 174.1, 164.4, 163.8, 161.1, 156.1, 137.5, 133.9, 130.9, 128.8, 128.3, 99.2, 89.9, 29.9, 28.7, 24.3, 12.7; IR (neat cm-1) 3401, 3312, 3159, 2970, 2933, 2871, 2222, 1623, 1563, 1427, 802, 740, 687; HRMS (ESI, M++H) m/z 345.1817 (calculated for C20H21N6, 345.1822); HPLC (a) tR=6.7 mins, 99.6%, (b) tR=7.6 mins, 99.6%

The chemical industry reduces the impact on the environment during synthesis 514854-13-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wright, Dennis L.; Anderson, Amy C.; Sormunen, Grant; US2015/225353; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 145783-15-9 ,Some common heterocyclic compound, 145783-15-9, molecular formula is C7H9Cl2N3S, 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.

A mixture of (1S,2S,3R,5S)-3-amino-5-(2-hydroxyethoxy)cyclopentane-1,2-diol (OLA; 1.06 g, 6 mmol), 4,6-dichloro-2-(propylthio)pyrimidin-5-amine (CLINA; 1.43 g, 6 mmol), triethylamine (1.09 g, 7.8 mmol) and polyethyleneglycol PEG400 (2 mL) was stirred for 48 h at 75 C. The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (25 mL) and evaporated under reduced pressure to give a resinous material which solidified upon trituration in n-hexane (25 mL). After filtration there was obtained OLACINA as a grey powder (2.0 g, 88% yield): 13C NMR (DMSO-d 6, 125 MHz) delta 13.3, 22.8, 32.2, 34.7, 54.8, 60.4, 69.8, 72.4, 75.2, 82.4, 119.9, 137.5, 152.5, 155.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,145783-15-9, its application will become more common.

Reference:
Patent; LEK Pharmaceuticals d.d.; The designation of the inventor has not yet been filed; EP2607355; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 36847-10-6, name is 4,6-Dibromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 4,6-Dibromopyrimidine

35.7g in a dry 2L three-necked flask 4.6-dibromopyrimidine and 27.9 g 3-aminobiphenyl, Then dry and degassed 800 mL of toluene was added as a solvent. Add 43.2g of sodium tert-butoxide, 0.67g catalyst palladium acetate (2% mol) and 3.7g Ligand 1,1′-binaphthyl-2,2′-bisdiphenylphosphine (BINAP, 4% mol). The temperature was raised to 110C and the reaction ended overnight. Cool to room temperature, add activated carbon adsorption, suction filtration, remove solvent, Recrystallization from toluene and ethanol, 33.3 g of intermediate K was obtained (yield 68%).

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, 36847-10-6, 4,6-Dibromopyrimidine.

Reference:
Patent; Nanjing Gao Guang Semiconductor Materials Co., Ltd.; Jin Zhenyu; Qian Chao; Gao Penghui; Wang Xiaowei; (62 pag.)CN107686484; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 36082-50-5, Adding some certain compound to certain chemical reactions, such as: 36082-50-5, name is 5-Bromo-2,4-dichloropyrimidine,molecular formula is C4HBrCl2N2, 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 36082-50-5.

General procedure: Heteroaryl chloride (1.0 eq), the corresponding amino alcohol (1.1 eq) and triethylamine (1.5 eq), were dissolved in n-BuOH (1 mL). The resulting reaction mixture was degassed with argon and irradiated in a commercial microwave apparatus at 125 C (30 W) for 1 h. Upon completion the solvent was removed under reduced pressure. The residue was purified by flash column chromatography (methanol : dichloromethane; 1:9) to afford the title compound.

According to the analysis of related databases, 36082-50-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gill, Daniel M.; Iveson, Matthew; Collins, Ian; Jones, Alan M.; Tetrahedron Letters; vol. 59; 3; (2018); p. 238 – 242;,
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Pyrimidine – Wikipedia

Application of 1211443-61-6, 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 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

Preparation of 3-[6-(7-Cyclopentyl-6-dimethylcarbarnoyl-7H-pyrrolo[2,3-d]pyrirri.d.n-2- ylamino)-pyridazine-3-carbonyl]-3,8-diaza-bicyclo[3.2.1 ]octane-8-carboxylic acid tert- butyl ester. In a 4 mL microwave vial 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine- 6-carboxylic acid dimethylarnide (98 mg, 0.336 mmol), 3-(6-amino-pyridazine-3- carbonyl)-3,8-dtaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (112 mg, 0.336 mmol), BINAP (10.5 mg, 0.017 mmol), Cs2C03 (164 mg, 0.504 mmol) and Pd(OAc)z (3.8 mg, 0.017 mmol) were added together. The tube was capped and then purged with N2 three times. Dioxane (1.68 mL) was added and the capped tube was heated to 120C for 20 min in a microwave reactor. After cooling the reaction mixture was diluted with heptane resulting in the crude product precipitating out. The crude product was isolated by filtration, re-suspended in water and subjected to vigorous stirring and sonication. After re-isolating by filtration the product was purified by normal phase silicachromatography with a 0 to 20% eOH/EtOAc gradient which gave a light tan solid (115 mg, 0.195 mmol). MS m/z 590.6 (M+H)+.

According to the analysis of related databases, 1211443-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BRAIN, Christopher, Thomas; CHO, Young Shin; GIRALDES, John, William; LAGU, Bharat; LEVELL, Julian; LUZZIO, Michael; PEREZ, Lawrence, Blas; WANG, Yaping; YANG, Fan; WO2011/101409; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1189169-37-6, 1-(5-Bromopyrimidin-2-yl)ethanone, 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, Recommanded Product: 1-(5-Bromopyrimidin-2-yl)ethanone, blongs to pyrimidines compound. Recommanded Product: 1-(5-Bromopyrimidin-2-yl)ethanone

At -78 C, n-butyllithium (2.5 M, 0.294 mL, 0.735 mmol) was added to a THF (7.35 mL) solution containing Example 369.0. The resulting mixture was stirred 30 mm at -78 C. Next, a THF solution of 1-(5-bromopyrimidin-2-yl)ethanone (0.208 g, 1.04 mmol) was added at -78C. The reaction was continued at -78 C and allowed to slowly warm to room temp and stirred overnight. The reaction was then quenched with a saturated solution of NH4C1 and extracted with EtOAc (3×1 00 mL). After concentration by solvent removal from the combined organic layers, the reaction was purified on silica eluting with a hexane/EtOAc gradient (0-100%). Desired fractions were then pooled and concentrated in vacuo. The material was then subjected to the reaction conditions described in Example 229.2 to deliver the desired compound. LCMS-ESI (pos.) m/z:695.0, 697.0 (M+H)t

The synthetic route of 1189169-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 54738-73-7 ,Some common heterocyclic compound, 54738-73-7, molecular formula is C5H3BrN4O, 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.

3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-ol (Intermediate A) (15.08 g, 70.5 mmol) was suspended in 189 ml of phosphous oxychloride. Diethylaniline (19 ml, 119.4 mmol) was added and the resulting reaction mixture was heated to 106 C. for 2 hours. After cooling to room temperature, the solvent was removed and the resulting amber syrup was poured to 300 ml of ice-water. 20 minutes later, the aqueous layer was extracted with diethyl ether (500 ml*4). The combined organic layer was washed, dried and evaporated to give 6.87 g of 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine as light yellow solid. 1H NMR (DMSO) 8.857 (s 1H), 14.84 (bs, 1H); LC/MS (MH+=233).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54738-73-7, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6921763; (2005); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1211443-61-6, 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 1211443-61-6 as follows.

A mixture of 2-chloro-7-cyclopentyl–N, N- dimethyl -7H- pyrrolo [2,3-d] pyrimidine-6-carboxamide (200mg, 0.68mmol), 5- (2- oxazolyl -7- aza-spiro [3.5]Nonane-1-yl) -2-amino-pyridine (0.17g, 0.78mmol), Cs2CO3 (0.20g, 1mmol), BINAP (20mg, 0.03mmol) andPd (OAc) 2 (10mg, 0.03mmol) was added mixed in 1,4-dioxane (30mL), purged with N2 at 95 react overnight.The reaction solutionAfter cooling, water was added (20 mL), and extracted with dichloromethane (40mL × 3), the organic phase was washed with water (15mL) washed with saturated brine (15mL) wash,Dried over anhydrous sodium sulfate, filtered, concentrated and the crude product is purified by silica gel column chromatography (methylene chloride / methanol (V / V) = 20/1), with methanolRecrystallized yellow solid (50mg, 15.4%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1211443-61-6, its application will become more common.

Reference:
Patent; East Sunshine Pharmaceutical Co., Ltd.; Liu, Bing; Zhang, Yingjun; Nie, Linlin; Bai, Shun; Zheng, Changchun; Nie, biao; Li, Zhiyong; Tan, Yumei; (61 pag.)CN105294737; (2016); A;,
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Pyrimidine – Wikipedia

Electric Literature of 15400-57-4, Adding some certain compound to certain chemical reactions, such as: 15400-57-4, name is Methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate,molecular formula is C8H10N2O3S, 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 15400-57-4.

A mixture of of 2.2 g of methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate, 15 g of Raney nickel (washed with methanol to remove water) and 200 mL of methanol was stirred under 1 atm hydrogen overnight. Conversion was incomplete by LCMS so the mixture was filtered and treated with 15 g of fresh Raney nickel under hydrogen overnight. After filtration and concentration under reduced pressure, purification by flash chromatography (0%-10% ethyl acetate in hexanes) gave the prodcut as white crystalline solid: MS (m+1) = 169.1; 1H NMR (400 MHz, CDC13) 9.0 (s, IH), 8.82 (s, IH), 4.1 (s, 3H), 3.9 (s, 3H).

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. 15400-57-4, Methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2007/67511; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22177-99-7, 4-(6-Chloro-2-methylpyrimidin-4-yl)morpholine, 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, 22177-99-7, blongs to pyrimidines compound. Quality Control of 4-(6-Chloro-2-methylpyrimidin-4-yl)morpholine

2-Methyl-4-chloro-6-morpholino-pyrimidine (10.7 g.; 50 mmol) was dissolved in tetrahydrofuran (200 mL). The reaction was chilled to -78C under an inert atmosphere. A solution of n-butyllithium in hexanes (25 mL, 2.5M, 62.50 mmol) was added, and the reaction mixture was stirred for thirty minutes. A solution of isobutylene oxide 6.6 mL, 75 mmol) was added, and the reaction was allowed to warm to room temperature while stirring overnight. The solvent was removed under reduced pressure, and the crude material was dissolved in methylene chloride (200 mL) and washed with saturated ammonium chloride (2×50 mL), dried with sodium sulfate, and evaporated to dryness. The compound was purified by column chromatography to give 4-(4-chloro-6-morpholin- 4-yl-pyrimidin-2-yl)-2-methyl-butan-2-ol (6.2 g., 21.7 mmol).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22177-99-7, its application will become more common.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2006/124662; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia