Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Propionitrile | HCID 7854 | — |
| Reactant | HCID 58128680 | HCID 58128680 | — |
| Reactant | HCID 58128704 | HCID 58128704 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 70794788 | HCID 70794788 | 48.7% |
Reaction Steps
(S)-4-(4-Fluoro-phenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid chloride, (230 mg), prepared as in Example 1, was added to a solution of 163 mg of 2-methyl-5-(4-methyl-pyrazol-1-yl)-phenylamine, 10 mL propionitrile, and 0.1 mL pyridine. The resulting solution was heated at 100° for 30 minutes, then cooled to 50° and diluted with 5 mL water and 10 mL toluene. The mixture was vigorously stirred at 50° and the layers were separated. The warm toluene layer was washed with saturated sodium bicarbonate, and then concentrated under reduced pressure to a brown residue, which was triturated with 2 mL toluene and filtered. The resulting solid was recrystallized from ethanol/water to yield 175 mg of (S)-4-(4-fluoro-phenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid[2-methyl-5-(4-methyl-pyrazol-1-yl)-phenyl]-amide, MS (M+H)=420.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08435990B2 |
|---|
| Source dataset | uspto-grants-2013_05 |
|---|
| ORD ID | ord-bb28ffed4a534993a3e35d0d47fbb405 |
|---|
| Source note | uspto-grants-2013_05 |
|---|