HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propargyl alcohol → 3-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-2-propyn-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propargyl alcohol | HCID 7859 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-Bromo-4-chloro-7H-pyrrolo[2,3-D]pyrimidine | HCID 45789827 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Product | 3-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-2-propyn-1-ol | HCID 90083562 | 31% |
Reaction Steps
A mixture comprising 3.00 g (12.9 mmol) 6-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (CAS-No: 784150-41-0), 90 mL tetrahydrofuran, 3.0 mL prop-2-yn-1-ol, 246 mg copper(I) iodide, 746 mg tetrakis(triphenylphosphine)palladium(0) and 3.93 mL N,N-diisopropylethylamine was heated at 80° C. for 4 hours. Water was added and the mixture extracted with ethylacetate/methanol (8:2). The organic layer was washed with brine and dried over sodium sulfate. After filtration and removal of the solvents the residue was purified by chromatography to give 833 mg (31%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09382255B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-1618b8364f504ed0a1a3c6b0504bf920 |
| Source note | uspto-grants-2016_07 |