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CAS No. : | 65195-35-9 | MDL No. : | MFCD01028678 |
Formula : | C7H9N3O2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | OBBDJDIJXFWRJK-UHFFFAOYSA-N |
M.W : | 167.17 | Pubchem ID : | 12454717 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302 | Packing Group: | |
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 |
---|---|---|
59% | for 2h;Heating / reflux; | Compound 21 (0.72 g, 4.3 mmol) was mixed with 8 mL of acetic anhydride and the reaction mixture was stirred under reflux for 2 h until no starting material was observed by TLC (4:1 EtOAc/hexanes). The reaction mixture was concentrated in vacuo and the product was purified by flash chromatography (CH2Cl21EtOAc) to yield 0.53 g of compound 22 in 59% yield. |
59% | for 2h;Reflux; | Ethyl 4-acetamidopyrimidine-5-carboxylate (22): Compound 21 (0.72 g, 4.3 mmol) was mixed with 8 mL of acetic anhydride and the reaction mixture was stirred under reflux for 2 h until no starting material was observed by TLC (4:1 EtOAc/hexanes). The reaction mixture was concentrated in vacuo and the product was purified by flash chromatography (CH2Cl2/EtOAc) to yield 0.53 g of compound 22 in 59% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sulfuric acid; for 72h;Heating / reflux; | Compound 20 (1.0 g, 7.2 mmol) was mixed with 15 mL of EtOH and 1 mL of H2SO4 (conc.). The suspension was left stirring under reflux conditions for 72 h. The solvent was removed under reduced pressure and the residue was poured over ice, stirred for 1 h and neutralized with Na2CO3 (sat.). The product was extracted into CHCl3 (3×70 mL) and combined organic layers were washed with brine and dried over Na2SO4. Concentration under reduced pressure gave 0.76 g of compound 21 in 63% yield. |
63% | With sulfuric acid; for 72h;Reflux; | Ethyl 4-aminopyrimidine-5-carboxylate (21): Compound 20 (1.0 g, 7.2 mmol) was mixed with 15 mL of EtOH and 1 mL of H2SO4 (conc.). The suspension was left stirring under reflux conditions for 72 h. The solvent was removed under reduced pressure and the residue was poured over ice, stirred for 1 h and neutralized with Na2CO3 (sat.). The product was extracted into CHCl3 (3×70 mL) and combined organic layers were washed with brine and dried over Na2SO4. Concentration under reduced pressure gave 0.76 g of compound 21 in 63% yield. |
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