HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tributylphosphine → 4'-{[4-Butyl-2-methyl-6-oxo-1-(1,3-thiazol-2-ylmethyl)-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | 1,1'-(Azodicarbonyl)dipiperidine | HCID 73042 | — |
| Reactant | 1,3-Thiazol-2-ylmethanol | HCID 2795213 | — |
| Reactant | 4'-[(4-Butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile | HCID 135401222 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4'-{[4-Butyl-2-methyl-6-oxo-1-(1,3-thiazol-2-ylmethyl)-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile | HCID 57460255 | 75.5% |
Reaction Steps
A mixture of 4′-[(4-butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (1 g), 1,1′-(azodicarbonyl)dipiperidine (1.41 g), tributylphosphine (1.74 mL), 1,3-thiazol-2-ylmethanol (0.48 g) and tetrahydrofuran (50 mL) was stirred at room temperature for 4 hr. The reaction mixture was concentrated. The residue was diluted with ethyl acetate, washed with water and then 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 as a colorless solid (0.96 g, 75%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07998968B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-e1300d3d0ad0413fa8a7da3d2ace0630 |
| Source note | uspto-grants-2011_08 |