HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bromoacetonitrile → HCID 86650724, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bromoacetonitrile | HCID 11534 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | (6s)-6-(4-Cyano-2-Methylsulfonyl-Phenyl)-4-Methyl-2-Oxidanylidene-3-[3-(Trifluoromethyl)phenyl]-1,6-Dihydropyrimidine-5-Carbonitrile | HCID 42642360 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86650724 | HCID 86650724 | 68.1% |
Reaction Steps
The reaction was carried out under argon. (4S)-4-[4-Cyano-2-(methylsulfonyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (115 mg, 250 μmol) was initially charged in THF (1 ml) at 0° C., sodium hydride (14 mg, 350 μmol; 1.4 eq.) was added and the mixture was stirred for 20 min. After addition of bromoacetonitrile (50 mg, 376 μmol; 1.5 eq.), the mixture was stirred at RT for 120 min. The reaction mixture was then purified directly by preparative HPLC (column: Gromsil, C-18 5 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→75:25). This gave the title compound as a colorless solid (85 mg, 68% of theory).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08889700B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-bb14376b5f3c4ad0b0907e14a77fee4c |
| Source note | uspto-grants-2014_11 |