HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl iodide → 5-(N-Boc-amino)-2-methoxy-4-methylpyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | N,N,N',N'-Tetramethylethylenediamine | HCID 8037 | — |
| Reactant | tert-Butyl (6-methoxypyridin-3-yl)carbamate | HCID 2763103 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | 5-(N-Boc-amino)-2-methoxy-4-methylpyridine | HCID 22612546 | — |
Reaction Steps
41.7 ml of 1.6M n-butyllithium in hexane and 7.7 g of TMEDA are added, under nitrogen, to 5 g of 5-(N-Boc-amino)-2-methoxypyridine, at −60° C. The medium turns yellow. The mixture is left stirring for 4 hours, allowing the temperature to return to −10° C., and a pale yellow. precipitate forms. The mixture is recooled to −40° C. and 4.7 g of methyl iodide are then added. The medium is allowed to return to RT and is then poured into water and extracted with EtOAc, and the extracts are dried and evaporated. The residue is chromatographed on silica, eluting with cyclohexane/EtOAc (85/15; v/v).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06380230B1 |
| Source dataset | uspto-grants-2002_04 |
| ORD ID | ord-58ae9d71aa834a018ca78afe6de94408 |
| Source note | uspto-grants-2002_04 |