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CAS No. : | 6490-42-2 | MDL No. : | MFCD00136723 |
Formula : | C6H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KPLDRYODCDLNHB-UHFFFAOYSA-N |
M.W : | 140.14 | Pubchem ID : | 4183135 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
14.0 g (20%) | EXAMPLE 36 44 Grams of N-ethylurea and 105 g of β,β-diethoxypropionic acid ethyl ester were added to a solution of 15.0 g of sodium in 700 ml of ethanol. The yellow solution was then heated for 3 hours at 25 and subsequently boiled under reflux for 15 hours. The mixture was evaporated in vacuo and the residue dissolved in 300 ml of water, cooled to 0 and acidified with 100 ml of concentrated hydrochloric acid. A crystalline intermediate precipitated out (43 g) and was filtered off under vacuum, washed with 100 ml of ice-water and subsequently heated to 80-100 in 250 ml of water until conversion into the desired water-soluble 1-ethyl-uracil is complete. The solution was evaporated in vacuo at 40 and the remaining residue recrystallized from ethanol/ether; yield 14.0 g (20%) of colorless 1-ethyl-uracil; melting point 150 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.5 g (42%) | With pyridine; diphosphorus pentasulfide; In ethanol; water; acetic acid; | Chlorine was led into a solution of 9.9 g of 1-ethyl-uracil in 150 ml of glacial acetic acid until iodine-potassium-starch paper reacted positively and 1-ethyl-uracil was no longer detectable by thin-layer chromatography (ca. 0.5 hours). The mixture was evaporated in vacuo at 40 and the crystalline residue recrystallized from 300 ml of ethanol; yield 10.0 g (81%) of colorless, fine needles of 1-ethyl-5-chlorouracil; melting point 244-247. 1.74 Grams of 1-ethyl-5-chlorouracil were mixed with 4.44 g of phosphorus pentasulfide and 0.1 ml of water and the mixture treated with 30 ml of pyridine and boiled at reflux for 3.75 hours. The mixture was then evaporated in vacuo at 40, the residue suspended in 30 ml of water and treated with 30 ml of 2-N hydrochloric acid. the crystals obtained were filtered off under suction, washed with water and recrystallized from 1-ethyl-5-chloro-1,2-dihydro-4-mercapto-2-oxo-pyrimidine; melting point 217-220. In a manner analogous to that described in Example 1 6.27 g of <strong>[58-71-9]<strong>[58-71-9]cephalothin sodium</strong> salt</strong> were reacted 3.04 g of 1-ethyl-5-chloro-1,2-dihydro-4-mercapto-2-oxo-pyrimidine prepared above to give (7R)-3-[[(1-ethyl-5-chloro-1,2-dihydro-2-oxo-4-pyrimidinyl)-thio]methyl]-7-[2-(2-thienyl)-acetamido]-3-cephem-4-carboxylic acid as the sodium salt; yield 3.5 g (42%); melting point from 185 (decomposition); [alpha]D20 = -95.2 (c = 0.394 in water). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | General procedure: To a double-necked round bottom flask (100mL), equipped with a condenser, it was added a mixture of KI (1.5mmol), P2O5 (1.5mmol) and the desired alcohol (1mmol) in DMF (5mL). The reaction mixture was stirred at r.t. for 30min. Next, the considered nucleobase (1mmol), K2CO3 (1mmol) and Et3N (1mmol) were added and the reaction mixture was heated to reflux for a further 6.5-10.5h (until TLC indicated no further progress in reaction, Table5). The solvent was then evaporated at reduced pressure, and the remaining foam was dissolved in chloroform (150mL) and washed with water (2×150mL). The organic layer was dried on Na2SO4 (1g) and evaporated. The product was purified using short column chromatography on silica gel eluting with proper solvents. |
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