HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triacetoxyperiodinane → {3-oxo-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}acetonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triacetoxyperiodinane | HCID 159087 | — |
| Reactant | 3-Hydroxy-1-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile | HCID 67017183 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | {3-oxo-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}acetonitrile | HCID 69675509 | — |
Reaction Steps
To a solution of {3-hydroxy-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}acetonitrile (1.62 g, 3.82 mmol) in DCM (50 mL) at 0° C. was added Dess-Martin periodinane (2.1 g, 5.0 mmol). After stirring for 2 hours, the reaction solution was diluted with ether and saturated NaHCO3 solution. The aqueous layer was extracted with ethyl acetate three times. The combined extracts were washed with brine, dried over sodium sulfate, decanted and evaporated. The crude was used in the next step without purification. LCMS (M+H)+: 423.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08933085B2 |
| Source dataset | uspto-grants-2015_01 |
| ORD ID | ord-cf28eb334e95448e96c1b3155e5f6f79 |
| Source note | uspto-grants-2015_01 |