Category: 344-14-9

Adding a certain compound to certain chemical reactions, such as: 344-14-9, name is Dimethyl 2-fluoromalonate, belongs to esters-buliding-blocks compound, 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 344-14-9, Product Details of 344-14-9

Part A: 5-Fluoro-6-hydroxy-2,4(1H,3H)-pyrimidinedione. A mechanically stirred solution of urea (60.06 g, 1 mol) and dimethyl fluoromalonate (150.1 1 g, 1 mol) in methanol (1 L) was treated with 25 wt% NaOMe in methanol (-4.6M, 435 mL, 2 mol). The mixture was refluxed for 3 h and then allowed to cool to room temperature. The mixture was filtered, the wet cake was dissolved in warm water (-1.2L), and the resulting aqueous solution was acidified with concentrated aqueous HCI(-160 mL) to pH = 2 while stirring over 1 h. The mixture was allowed to cool to room temperature, and the product was filtered and washed thoroughly with water, then dried under vacuum to give 5-fluoro-6-hydroxy-2,4(1 H,3H)-pyrimidinedione (80 g, 55%) as a white solid. LCMS: (M+H)+: 147.0.

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, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/61879; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 344-14-9, name is Dimethyl 2-fluoromalonate, belongs to esters-buliding-blocks compound, 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 344-14-9, Recommanded Product: Dimethyl 2-fluoromalonate

(R)-7-Fluoro-8-hydroxy-1 -((S)-1 -(4-methoxyphenyl)ethyl)-4- (trifluoromethyl)-3,4-dihydro-1 H-pyrimido[1 ,2-a]pyrimidin-6(2H)-one can be prepared in the following way. 30 g of methyl fluoromalonate and 10.8 g of anhydrous sodium methoxide are added, at ambient temperature and under an argon atmosphere, to a suspension of 12 g of (S)-1 -[(S)-1 -(4-methoxyphenyl)ethyl]- 4-trifluoromethyl-1 ,4,5,6-tetrahydropyrimidin-2-ylamine in 150 ml of methanol. The mixture obtained is then heated at reflux. After one hour of stirring at reflux, the reaction is complete according to the verification by LC/MS. After cooling, the reaction mixture is evaporated to dryness under reduced pressure. The residue obtained is taken up with 100 ml of cold water. 36% HCI is added dropwise to pH = 6. The solid formed is filtered off and then washed three times with ethyl ether. The solid is oven-dried under vacuum in the presence of P2O5, so as to give 15 g of (R)-7-fluoro-8-hydroxy-1 -((S)-1 -(4- methoxyphenyl)ethyl)-4-(trifluoromethyl)-3,4-dihydro-1 H-pyrimido[1 ,2- a]pyrimidin-6(2H)-one, which is used as it is in the next step.

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

Reference:
Patent; SANOFI; EL-AHMAD, Youssef; FILOCHE-ROMME, Bruno; LETALLEC, Jean-Philippe; MARCINIAK, Gilbert; RONAN, Baptiste; VIVET, Bertrand; WO2013/190510; (2013); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 344-14-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 344-14-9, name is Dimethyl 2-fluoromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 1Mixture of dimethyl fluoro[(1R,5R)-5-hydroxycyclopent-2-en-1-yl]propanedioate (8a) and dimethyl fluoro[(1S,5S)-5-hydroxycyclopent-2-en-1-yl]propanedioate (8b) 23.81 g (110.2 mmol) of a 25 w/w % methanol solution of sodium methoxide (NaOMe) was added to a methanol (90.4 mL) solution of 18.19 g (121.2 mmol) of dimethyl fluoropropanedioate (7) over 3 minutes while keeping the internal temperature between 25 C. and 38 C. After stirring the solution thus obtained for 15 minutes, 4.52 g (55.1 mmol) of 6-oxabicyclo [3.1.0] hex-2-ene (6) was added thereto over 2 minutes while keeping the internal temperature between 25 C. and 38 C. After stirring at room temperature for 1 hour, 45 mL of a saturated ammonium chloride aqueous solution was added over 10 minutes while keeping the internal temperature between 26 C. and 35 C. The reaction mixture was concentrated under reduced pressure, most of the methanol was removed by evaporation, and 108 g of a brown solution containing solids was obtained. After extraction with 136 mL of ethyl acetate was carried out twice, washing with 45 mL of water was carried out. After the organic layer was concentrated under reduced pressure, 100 mL of toluene was added, and concentration under reduced pressure was carried out again. The concentrated residue was purified by flash silica gel column chromatography (eluent:toluene/ethyl acetate), thus giving 7.21 g of a mixture of the compound of the formula 8a and the compound of the formula 8b as a yellow oily substance.1H NMR (500 MHz, DMSO-d6): delta (ppm) 2.13-2.17 (m, 1H), 2.56 (dddd, J=2.2, 4.3, 7.1, 17.2 Hz, 1H), 3.32-3.40 (m, 1H), 3.77 (s, 3H), 3.79 (s, 3H), 4.20 (m, 1H), 5.04 (d, J=6.1 Hz, 1H), 5.47 (ddd, J=2.1, 4.3, 6.1 Hz, 1H), 5.85 (ddd, J=2.2, 4.4, 6.1 Hz, 1H). 13C NMR (125 MHz, DMSO-d6): delta (ppm) 41.93, 53.39 (d, J=19.5 Hz), 58.70 (d, J=20.8 Hz), 70.43 (d, J=2.6 Hz), 93.55, 95.14, 125.59, 133.32, 165.42 (d, J=15.6 Hz), 165.62 (d, J=14.3 Hz). 19F NMR (470 MHz, DMSO-d6): delta (ppm) -172.43, -172.36. HRMS(ES)m/z: [M+Na]+ calcd for CHH13O5FNa; 255.0645, found 255.0635. IR (neat) 3528, 3408, 2960, 1755, 1438, 1284, 1253, 1173, 1111, 1068, 1031, 936, 838, 787, 722, 668, 415 cm-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, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; US2012/232304; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 344-14-9,Some common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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.

Example 224 Synthesis of dimethyl 2-((2-((4-(tert-butoxycarbonyl)-1H-1,2,3-triazol-1-yl)methyl)-6-cyclopropylimidazo[1,2-a]pyridin-8-yl)methyl)-2-fluoromalonate. To a solution of compound dimethyl 2-fluoromalonate (0.54 g, 3.6 mmol) in anhydrous DMF (10 mL) was added NaH (140 mg, 3.6 mmol, 60% in mineral oil) and the reaction was stirred at 0 C. for 0.5 h under N2 atmosphere. Then the solution of tert-butyl 1-((8-(chloromethyl)-6-cyclopropylimidazo[1,2-a]pyridin-2-yl)methyl)-1H-1,2,3-triazole-4-carboxylate (1 g, 2.5 mmol) in DMF (2 mL) was added, The resulting mixture was stirred at 80 C. for 16 h. The reaction was quenched with saturated aqueous NH4Cl solution (20 mL), and extracted with ethyl acetate (100 mL*2). The combined organic phases were dried over Na2SO4, evaporated to give the crude, which was purified with silica gel chromatography (DCM/MeOH=100/1) to give the dimethyl 2-((2-((4-(tert-butoxycarbonyl)-1H-1,2,3-triazol-1-yl)methyl)-6-cyclopropylimidazo[1,2-a]pyridin-8-yl)methyl)-2-fluoromalonate (1.1 g, 85%) as a yellow solids. ESI-MS [M+H]+: 502.3.

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

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 344-14-9, The chemical industry reduces the impact on the environment during synthesis 344-14-9, name is Dimethyl 2-fluoromalonate, I believe this compound will play a more active role in future production and life.

General procedure: [Pd(C3H5)Cl]2 (0.004 mmol, 4 mol%), [6-(allyloxymethyl)-N-(2-((R)-((S)-1-(3,5-dimethoxyphenyl)propyl)sulfinyl)phenyl)picoli-namide] (6b, 0.008 mmol, 8 mol%), and (E)-1,3-disubstituted allyl acetates 7 (0.1 mmol) were dissolved in THF (2.0 mL) in a dry Schlenk tube filled with argon. The reaction mixture was stirred for 30 min at room temperature. Then Cs2CO3 (3.0 equiv) and dimethyl 2-fluoromalonate 8 (0.3 mmol, 3.0 equiv) were added. After the completion of the reaction monitoring by TLC, the crude reaction mixture was filtrated with celite and the solvent was removed under reduced pressure. The crude residue was purified by flash column chromatography (petroleum ether/ethyl acetate) to give the desired products 9.

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, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Min; Zhao, Mingzhu; Zheng, Purui; Zhang, Hongbo; Zhao, Xiaoming; Journal of Fluorine Chemistry; vol. 189; (2016); p. 13 – 21;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 344-14-9, 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. 344-14-9, name is Dimethyl 2-fluoromalonate, This compound has unique chemical properties. The synthetic route is as follows.

Dimethyl 2-fluoromalonate (77.00g, 0.80mol, 2.0eq.) Was dissolved in 1L of tetrahydrofuran, cooled to -40 , 1M NaHMDS tetrahydrofuran solution (800mL, 0.80mol, 2.0eq. ), After stirring for 1h, add 400mL of a compound of formula (50g, 0.40mol, 1.0eq.) In tetrahydrofuran solution 400mL, return to room temperature after completion of the dropwise reaction for 2h, add 500mL of saturated ammonium chloride aqueous solution to separate, organic The phase was washed with saturated brine, dried, concentrated, column chromatography (petroleum ether / ethyl acetate), and concentrated to obtain 99.7 g of the compound of formula III, with a yield of 45.1%.

The chemical industry reduces the impact on the environment during synthesis Dimethyl 2-fluoromalonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nanjing Furunkaide Bio-pharmaceutical Co., Ltd.; Zhang Leiliang; Xu Feng; (16 pag.)CN110963955; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

344-14-9, These common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, 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.

First, put a stir bar in a 35 mL sealed tube, and then add methyl propargyl ether (28 muL, 0.33 mmol), 0.9 mL tetrahydrofuran (0.9 mL), and 2-chloroacetamidoquinoline (66.2 mg, 0.3 mmol), dimethyl 2-fluoromalonate (70.4 mg, 0.45 mmol). To the mixed solution were added CuI (5.7 mg, 0.03 mmol) and Cs2CO3 (117.3 mg, 0.36 mmol) in this order. The glass tube was filled with N2 for 3 minutes, the air was fully expelled, the nozzle was sealed with a cock, and the reaction was stirred at 800C for 1.5 hours. After the reaction was completed, the system was cooled to room temperature, 2 ml of distilled water was added to the reaction system, and ethyl acetate was used. After extraction, the organic phases were combined, and the solvent of the organic phase was distilled off under reduced pressure. 86.1 mg of the product was separated by silica gel column chromatography in 4d, and the yield was 71%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 344-14-9.

Reference:
Patent; Anyang Normal University; Lv Yunhe; Pu Weiya; Wang Xin; Wang Xiaoxing; (15 pag.)CN110627718; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

344-14-9, The chemical industry reduces the impact on the environment during synthesis 344-14-9, name is Dimethyl 2-fluoromalonate, I believe this compound will play a more active role in future production and life.

General procedure: [Pd(C3H5)Cl]2 (0.004 mmol, 4 mol%), [6-(allyloxymethyl)-N-(2-((R)-((S)-1-(3,5-dimethoxyphenyl)propyl)sulfinyl)phenyl)picoli-namide] (6b, 0.008 mmol, 8 mol%), and (E)-1,3-disubstituted allyl acetates 7 (0.1 mmol) were dissolved in THF (2.0 mL) in a dry Schlenk tube filled with argon. The reaction mixture was stirred for 30 min at room temperature. Then Cs2CO3 (3.0 equiv) and dimethyl 2-fluoromalonate 8 (0.3 mmol, 3.0 equiv) were added. After the completion of the reaction monitoring by TLC, the crude reaction mixture was filtrated with celite and the solvent was removed under reduced pressure. The crude residue was purified by flash column chromatography (petroleum ether/ethyl acetate) to give the desired products 9.

The chemical industry reduces the impact on the environment during synthesis Dimethyl 2-fluoromalonate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Min; Zhao, Mingzhu; Zheng, Purui; Zhang, Hongbo; Zhao, Xiaoming; Journal of Fluorine Chemistry; vol. 189; (2016); p. 13 – 21;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 344-14-9, name is Dimethyl 2-fluoromalonate, This compound has unique chemical properties. The synthetic route is as follows., 344-14-9

General procedure: A test tube chargedwith MS 3A (40.0 mg, 200 mg/mmol) was flame-dried under reduced pressure using a heat gun. After cooling to room temperature, argon was re-filled, Schiff base 1 (11.1 mg, 0.02 mmol), THF (0.2 mL) andGd(OiPr)3 (0.2 M THF solution, 0.1 mL, 0.02 mmol) were added. The mixture was stirred at roomtemperature for 30 min to afford yellow suspension. THF was, then, removed under reduced pressure. Tothe test tube were added Y(OTf)3 (10.7 mg, 0.02 mmol) and THF (0.20 mL), and the mixture was stirred at room temperature for 30 min to afford the Gd(OiPr)3/Y(OTf)3/Schiff base = 1:1:1 catalyst in THF.Then, DMAP (2.4 mg, 0.02 mmol) was added, and THF was removed under reduced pressure. After drying the residue under reduced pressure for 1 h at room temperature, toluene (0.2 mL) and Et2O (0.4mL) were added. To the resulting red suspension were added 2-fluoromalonate 3 (0.35 mmol, 1.7 equiv)and meso-aziridine 2 (0.20 mmol, 1.0 equiv), and the mixture was stirred for 17-72 h at 40 C. After themixture was cooled to room temperature and diluted with AcOEt, saturated EDTA?2Na aq. was added.The organic layer was separated, and the aqueous layer was extracted with AcOEt and the organic layers were washed with brine. The organic layers were dried over Na2SO4. After filtration and evaporation, the obtained crude mixture was purified by silica gel column chromatography (AcOEt/hexane/CH2Cl2) togive a corresponding product.

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.

Reference:
Article; Fukagawa, Seiya; Xu, Yingjie; Anada, Masahiro; Yoshino, Tatsuhiko; Matsunaga, Shigeki; Heterocycles; vol. 94; 7; (2017); p. 1337 – 1350;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 344-14-9, name is Dimethyl 2-fluoromalonate, I believe this compound will play a more active role in future production and life. 344-14-9

Part B 2-(Difluoromethyl)-5-fluoro-6-hydroxy-4(1 H)-pyrimidinone Sodium metal (0.91 g, 40 mmol) was dissolved in MeOH (100 mL) to form sodium methoxide. 2,2-Difluoroethanimidamide HCI (1 .73 g, 13 mmol) was added followed by dimethyl fluoropropanedioate (2.0 g, 13 mmol). The resulting solution was stirred at 80 C for 3 hours, then cooled to room temperature. Aqueous HCI (6 mL, 6M, 36 mmol) was added and the resulting mixture was concentrated in vacuo. The remaining solid was washed with cold water and filtered yielding 2-(difluoromethyl)-5- fluoro-6-hydroxy-4(1 H)-pyrimidinone (1.43 g, 61 %)

The chemical industry reduces the impact on the environment during synthesis 344-14-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO. 2) LIMITED; AUBART, Kelly, Marshall; GILLIAN, Jason, Michael; QIN, Donghui; MCKEOWN, Robert, Rahn; WILLIAMS, Glenn, R.; WO2013/82388; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics