HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 6-[1-(1-Methylpyrrolidin-3-yl)-4-phenyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | tert-butyl 3-[5-(4-aminothieno[2,3-d]pyrimidin-6-yl)-4-phenyl-1H-imidazol-1-yl]pyrrolidine-1-carboxylate | HCID 69197495 | — |
| Catalyst | Trifluoroacetic acid | HCID 6422 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 6-[1-(1-Methylpyrrolidin-3-yl)-4-phenyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine | HCID 10022422 | 28% |
Reaction Steps
A mixture of lithium aluminium hydride in THF (1M, 0.1 mL), THF (2 mL) and tert-butyl 3-[5-(4-aminothieno[2,3-d]pyrimidin-6-yl)-4-phenyl-1H-imidazol-1-yl]pyrrolidine-1-carboxylate (intermediate 102) (31 mg) was refluxed for 4 hours under an inert atmosphere. After addition of water and TFA (1 drop), the mixture was evaporated and the residue was purified by preparative RPHPLC (eluting with a gradient of MeCN and water containing 0.1% TFA) to afford the title compound as a colourless solid (5 mg, 28%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07427616B2 |
| Source dataset | uspto-grants-2008_09 |
| ORD ID | ord-a7219b19809e4c6baa966b053d79b2d4 |
| Source note | uspto-grants-2008_09 |