Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 5-Pyrimidinecarboxylic acid, 4-amino-2-(methylthio)-, ethyl ester | HCID 222666 | — |
| Reactant | 2-Chloro-6-methylphenyl isocyanate | HCID 268123 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58458121 | HCID 58458121 | 63.7% |
Reaction Steps
To a solution of 100 mg of ethyl 4-amino-2-(methylsulfanyl)pyrimidine-5-carboxylate in 4 mL of N,N-dimethylformamide, 56 mg of sodium hydride was added, and the resulting mixture was stirred at room temperature for 5 minutes. To the reaction mixture, 118 mg of 2-chloro-6-methylphenyl isocyanate was added, and the resulting mixture was stirred at room temperature for 1 hour. To the reaction mixture, ethyl acetate and a 1 N aqueous hydrochloric acid solution were added and the organic layer was separated. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, and then, the solvent was distilled off. The precipitated solid was solidified with methanol and collected by filtration, whereby 100 mg of the title compound was obtained as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08575179B2 |
|---|
| Source dataset | uspto-grants-2013_11 |
|---|
| ORD ID | ord-ff82b492940e4440aedaab102cd6c68f |
|---|
| Source note | uspto-grants-2013_11 |
|---|