HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetyl chloride → 1-(2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Aluminum(III) Chloride | HCID 6451240 | — |
| Reactant | 2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine | HCID 86637342 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-(2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethanone | HCID 86637343 | 96.7% |
Reaction Steps
To a solution of aluminium chloride (400 mg, 2.99 mmol) and acetyl chloride (711 uL, 10 mmol) in dichloromethane (2 mL) is added 2-chloro-7-(cyclopentyl)-7H-pyrrolo[2,3-d]pyrimidine (221 mg, 1.0 mmol) in dichloromethane (5 mL), dropwise. After 20 minutes saturated aqueous sodium bicarbonate is added to pH 9-10 and the solution is extracted with dichloromethane. The organic phase is dried, anhydrous Na2SO4 and concentrated to obtain 1-(2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethanone (255 mg, 97%) as an off-white amorphous solid (97%). 1H-NMR and LCMS.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08324225B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-7523e394e25448fb9bb3b856a09d5bac |
| Source note | uspto-grants-2012_12 |