HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrabutylammonium Fluoride → 1-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | 4-[2-Chloro-4-(1-ethyl-propylamino)-pyrimidin-5-yl]-but-3-yn-2-ol | HCID 86637349 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanol | HCID 73554661 | 52.7% |
Reaction Steps
To a solution of 4-[2-chloro-4-(1-ethyl-propylamino)-pyrimidin-5-yl]-but-3-yn-2-ol (0.23 g, 0.85 mmol) in THF (0.5 mL) is added 1M TBAF (4.3 mL). The reaction mixture is heated at reflux for 16 h, diluted with water, extracted with EtOAc. The extracts are dried over Na2SO4 and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, EtOAc/Hexane 1:3) to provide 0.12 g of 1-[2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethanol.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08324225B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-36f0704d68b54640ad4b8f0c8447139d |
| Source note | uspto-grants-2012_12 |