HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → (1S,2S,4R)-4-{-4-[(1R)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-(hydroxymethyl)cyclopentanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | N-[(1R)-2,3-Dihydro-1H-inden-1-yl]-7-[(4aS,6R,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine | HCID 66618085 | — |
| Solvent | Water | HCID 962 | — |
| Product | (1S,2S,4R)-4-{-4-[(1R)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-(hydroxymethyl)cyclopentanol | HCID 66618256 | 52.2% |
Reaction Steps
N-[(1R)-2,3-Dihydro-1H-inden-1-yl]-7-[(4aS,6R,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (70.0 mg, 0.145 mmol) was added to a solution of AcOH (0.742 mL, 13.0 mmol), THF (0.235 mL) and water (0.261 mL). The solution was stirred at rt for 4 days before being concentrated in vacuo. Silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM afforded the title compound (27.6 mg, 52%). LC/MS: Rt=0.94 min, ES+ 365 (FA standard).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08207177B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-b5f8e7c5e9ce45f4ba90ec2330fb4d2a |
| Source note | uspto-grants-2012_06 |