HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → ((S)-1-methanesulfonyl-piperidin-3-yl)-{5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | ((S)-1-methanesulfonyl-piperidin-3-yl)-{2-methylsulfanyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine | HCID 69812827 | — |
| Catalyst | Nickel | HCID 935 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | ((S)-1-methanesulfonyl-piperidin-3-yl)-{5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine | HCID 69811925 | 21.8% |
Reaction Steps
((S)-1-methanesulfonyl-piperidin-3-yl)-{2-methylsulfanyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine (400 mg, 0.728 mmol) was dissolved in dioxane (10 ml), ethanol (2 ml) and water (2 ml) and treated with 2 g of Raney Nickel (2000). This was refluxed for 16 hours. The reaction was filtered, evaporated and purified by silica gel chromatography (5% methanol/methylene chloride to give ((S)-1-methanesulfonyl-piperidin-3-yl)-{5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine (˜80 mg). MS (ES+): 504.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08618103B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-7c12f3862c7148e09f26c45bca9119fe |
| Source note | uspto-grants-2013_12 |