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CAS No. : | 35144-22-0 | MDL No. : | MFCD03788286 |
Formula : | C7H10N2O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZHPSNGCLCHWTRG-UHFFFAOYSA-N |
M.W : | 186.23 | Pubchem ID : | 2772382 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With water; chlorine; In dichloromethane; at 0℃; | 15.9 g (103 mmol) of 4,6-dimethyl-1-methylthiopyrimidine were introduced into 120 ml of dichloromethane and 110 ml of water.. chlorine gas was passed into saturation (yellow coloration) at 0 C. After the conversion was complete, excess chlorine was driven out with nitrogen, the aqueous phase was extracted with dichloromethane, and the collected organic phases were dried over magnesium sulfate.. The solution was concentrated, and the product (14 g, 73%) was crystallized by adding ether. Melting point: 79-80 C. 1H-NMR (270 MHz): 7.2 ppm (1H, s), 3.4 (3H, s), 2.6 (6H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55 g (130 mmol) of 2-hydroxy-3-(2-(3,4-dimethoxyphenyl)ethoxy-3,3-diphenylpropionic acid, dissolved in 150 ml of DMF, were added over the course of 15 minutes to 9 g (390 mmol) of lithium amide in 35 ml of DMF. 25 g (137 mmol) of 2-methylsulfone-4,6-dimethylpyrimidine [sic], dissolved in 75 ml of DMF, were slowly added dropwise to this, and the mixture was stirred at room temperature for 18 hours. For workup, the mixture was added to 2 l of ice-water and citric acid for neutralization. The crystals which separated out were filtered off with suction and washed with water. The moist crystals were dissolved in dichloromethane, the solution was dried over magnesium sulfate and filtered, and the solvent was distilled off. The oily residue was taken up in ether and extracted with 130 ml of 1 N sodium hydroxide solution, and the aqueous phase was neutralized with 130 ml of 1 N hydrochloric acid, whereupon crystals separated out. 64 g of product were isolated after drying. [00202] 1H-NMR (200 MHz): 7.3 ppm (10H, m), 6.7 (4H, m), 6.3 (1H, s), 3.9 (3H, s), 3.85 (3H, s), 3.7 (1H, dt), 3.6 (1H, dt), 2.8 (2H, t), 2.3 (6H, s). [00203] Melting point: 125-130 C. decomposition EI-MS: M+=528. [00204] (S)-2-(4,6-dimethylpyrimidin-2-yloxy)-3-(2-(3,4-dimethoxyphenyl)ethoxy-3,3-diphenylpropionic acid was prepared in a similar way from (S)-2-hydroxy-3-(2-(3,4-dimethoxyphenyl)ethoxy)-3,3-diphenylpropionic acid and 2-methylsulfone-4,6-dimethylpyrimidine [sic] in the presence of lithium amide. [alpha]20=111 (1; ethanol). |
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