HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → 6-Bromopyrazolo[1,5-a]pyrimidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Pyrazol-3-ylamine | HCID 74561 | — |
| Reactant | 2-Bromopropanedial | HCID 74945 | — |
| Product | 6-Bromopyrazolo[1,5-a]pyrimidine | HCID 22236701 | — |
| Product | 5-Bromopyrazolo[3,4-b]pyridine | HCID 40427454 | — |
Reaction Steps
A solution of 1H-pyrazol-5-amine x79 (25 g, 1 eq, 0.3 mol) and bromomalonaldehyde x9 (45.4 g, 1 eq, 0.3 mol) ethanol (250 ml) is refluxed for 2 hours. After cooling, the reaction mixture is stirred at room temperature overnight. The solvent is removed under reduced pressure and the crude is purified using chiral chromatography affording 5-bromo-1H-pyrazolo[3,4-b]pyridine x80 (yield: 2.1%; LC-MS (MH+): 198/200) and 6-bromopyrazolo[1,5-a]pyrimidine x81 (yield: 13.8%; LC-MS (MH+): 198/200).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08586623B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-869c857398004e52aac85fc783f972ca |
| Source note | uspto-grants-2013_11 |