Category: 344-14-9

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.

To a stirred solution of dimethyl fluoromalonate (1 mmol, 150.11 mg) in anhydrous methanol (10 ml) was added a solution of n-octylamine (1 mmol, 166 mul) in methanol (5 ml) drop wise over the period of one hour at room temperature. It was then further stirred at room temperature for two hours. The solution was rotary evaporated and the residue redissolved in ethyl acetate. The ethyl acetate solution was sequentially washed with 2 M HCI (2×10 ml) and saturated sodium chloride (1×15 ml) solution. Drying over MgSO4 and rotary evaporation of organic solvent gave white solid that was a mixture of bisamide and ethyl 4-aza-2-fluoro-3-oxododecanoate. Desired product was purified as a white solid by PLC in 40-60 petroleum ether – diethyl ether (3:2), (117 mg, 47%).TLC Rf 0.23, petroleum ether- diethyl ether (3:2)1H NMR (400 MHz, CDCI3) delta 0.88 (3H, t, J 6.4 Hz, (CH3(CH2)/), 1.29 (10H, m, CH3(CH2)5), 1.54 (2H, br s, CH3(CH2)5CH2), 3.32 (2H, m, J 6.6 Hz, CH3(CH2)6CH2), 3.9 (3H, s, OCH3), 5.28 (1 H, d, J 49.2, C(H)F), 6.42 (1 H, s, NH).

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; THE UNIVERSITY OF NOTTINGHAM; WO2007/135466; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 344-14-9, name is Dimethyl 2-fluoromalonate, A new synthetic method of this compound is introduced below., 344-14-9

General procedure: In a 50 mL two-necked flask containing dichloromethane (10 mL) were added the amine (17 mmol) followed by the aldehyde (15 mmol) and the resulting reaction mixture was allowed to stir at rt for 2 h, before the fluorinated dicarbonyl system (10 mmol) was added. The reaction mixture was stirred at rt for 16 h, evaporated and the residue dissolved in dichloromethane (20 mL), washed with distilled water (2¡Á20 mL), dried over magnesium sulfate and evaporated, to give the desired product. Further purification by distillation or column chromatography eluting from hexane/ethyl acetate was carried out when appropriate. Analytical and spectroscopic data for each individual compound are listed below. For NMR data only resonances of one diastereoisomer or conformer is given for clarity.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Lisse, Etienne; Sandford, Graham; Journal of Fluorine Chemistry; vol. 206; (2018); p. 117 – 124;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

344-14-9, Name is Dimethyl 2-fluoromalonate, 344-14-9, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

General procedure: In a 50 mL two-necked flask containing dichloromethane (10 mL) were added the amine (17 mmol) followed by the aldehyde (15 mmol) and the resulting reaction mixture was allowed to stir at rt for 2 h, before the fluorinated dicarbonyl system (10 mmol) was added. The reaction mixture was stirred at rt for 16 h, evaporated and the residue dissolved in dichloromethane (20 mL), washed with distilled water (2¡Á20 mL), dried over magnesium sulfate and evaporated, to give the desired product. Further purification by distillation or column chromatography eluting from hexane/ethyl acetate was carried out when appropriate. Analytical and spectroscopic data for each individual compound are listed below. For NMR data only resonances of one diastereoisomer or conformer is given for clarity.

Statistics shows that Dimethyl 2-fluoromalonate is playing an increasingly important role. we look forward to future research findings about 344-14-9.

Reference:
Article; Lisse, Etienne; Sandford, Graham; Journal of Fluorine Chemistry; vol. 206; (2018); p. 117 – 124;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

344-14-9, 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. 344-14-9, name is Dimethyl 2-fluoromalonate, A new synthetic method of this compound is introduced below.

(8R, 8S)-3-Fluoro-2-hydroxy-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H- pyrimido[1 ,2-a]pyrimidin-4-one can be prepared in the following way. 5.6 g of sodium methoxide are added to a suspension of 7 g of (4R,4S)-4-(trifluoromethyl)-1 ,4,5,6-tetrahydropyrimidin-2-ylamine hydrochloride in 35 ml of dimethyl fluoropropanedioate. After stirring the suspension for 3 hours at a temperature of 100C, the medium obtained is concentrated to dryness under reduced pressure. The residue is taken up in diethyl ether and then dried with suction under vacuum. The solid obtained is taken up in 14 ml of water, and the resulting mixture is cooled in ice, before acidification to pH 5-6 by addition of concentrated hydrochloric acid (25%). After 2 hours of stirring at a temperature of 0C and then overnight at a temperature of about 20C, the suspension is filtered and then the solid is dried with suction and dried under vacuum over P2O5. 6.5 g of (8R, 8S)-3- fluoro-2-hydroxy-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1 ,2- a]pyrimidin-4-one are obtained in the form of a yellow powder, the characteristics of which are the following: Mass spectrum (method A) (ES +/-) [M+H]+: m/z 254; [M-H]-: m/z 252; Tr (min) = 0.28

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:
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

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. 344-14-9, name is Dimethyl 2-fluoromalonate, A new synthetic method of this compound is introduced below., 344-14-9

Part A: 5-Fluoro-6-hydroxy-2-methylthio-4(1 H)-pyrimidinone To a stirred solution of 2-methyl-2-thiopseudourea sulfate (41.7 g, 0.15 mol) and dimethyl fluoromalonate (45 g, 0.30 mol) in MeOH (600 mL) at 0 C (ice bath) was added NaOMe (48.6 g, 0.90 mol) in portions. After the addition was complete, the ice bath was withdrawn and the reaction mixture was stirred at room temperature overnight. LCMS showed the formation of the desired pyrimidinone product. The reaction mixture was concentrated to near dryness under vacuum, diluted with water (50 mL), and acidified with 6N HCI (-150 mL) to ~pH 2 to precipitate the product. After filtration, the solid was washed with 1 N HCI (2 x 10 mL) and dried under vacuum to afford 5-fluoro-6- hydroxy-2-methylthio-4(1 H)-pyrimidinone (35.7 g, 68%) as a white solid. LCMS: (M+H)+: 177.3.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

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

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, 344-14-9

A. Preparation of 5-Fluoro-4,6-dihydroxy-2-pyrimidineamine (3) Sodium (257 mg, 11 mmol) was dissolved in absolute ethanol (50 ml) with stirring under argon. When the sodium had thoroughly dissolved, guanidine hydrochloride (2) (502 mg, 5 mmol) and diethyl fluoromalonate (1) (790 mg, 4.4 mmol) were added. The solution was left to stir at room temperature overnight. A condenser was then attached to the flask and the solution was refluxed under argon for 4.5 hours. The solution was cooled to room temperature and concentrated. The residue was redissolved in 20 ml hot H2 O and acidified to pH 4. The mixture was cooled on ice and the precipitate was collected, yielding (3) as a peach colored solid (618 mg, 96%): MS (70 eV, EI)m/z (relative intensity) 146(M+, 100), 18 (95), 172 (26), 17 (24), 300 (21); IR (mull, cm-1) 3363, 1695, 1601, 1420, 1208, 677, 666; UV (MeOH, nm) 206(3,840), 235(3,380), 270(11,600). Exact Mass Calcd for C4 H4 N3 O2 F: 146.0366. Found: 146.0371.

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; The Upjohn Company; US5373012; (1994); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics