HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium bisulfate → 4'-{[1-(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium bisulfate | HCID 516920 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 4'-{[1-(2,2-dimethyl-4-oxo-3,4-dihydro-2H-chromen-6-yl)-2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile | HCID 57460406 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4'-{[1-(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile | HCID 57460407 | 100% |
Reaction Steps
4′-{[1-(2,2-Dimethyl-4-oxo-3,4-dihydro-2H-chromen-6-yl)-2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile (7.0 g) was dissolved in methanol (35 mL) and tetrahydrofuran (35 mL), and sodium borohydride (0.61 g) was added at 0° C. After stirring for 30 min, 5% aqueous potassium hydrogen sulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound (7.0 g, 100%) as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07803940B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-164e41019e3945b092fc50f9725b5df9 |
| Source note | uspto-grants-2010_09 |