HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(((Tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile → 3-(aminomethyl)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methylpyridin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(((Tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile | HCID 68294809 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | Nickel | HCID 935 | — |
| Solvent | Ammonia | HCID 222 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 3-(aminomethyl)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methylpyridin-2(1H)-one | HCID 68294760 | 63% |
Reaction Steps
To a stirred solution of 4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (5.5 g, 19.7 mmol) in methanol (100 mL) and ammonia (30 mL) was added Raney nickel (quantitative) and the reaction mixture was stirred in presence of hydrogen under balloon pressure for 14 h. On completion, reaction mixture was filtered through celite and washed with methanol. Removal of the solvent under reduced pressure afforded the desired compound (3.5 g, 63%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08765732B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-80fb6c174169404a808252e5a23d91c4 |
| Source note | uspto-grants-2014_07 |