HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → HCID 178463588, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | tert-butyl N-(9-tritylpurin-6-yl)carbamate | HCID 70974658 | — |
| Reactant | 3-(1-bromoethyl)-4-(3,6-dihydro-2H-pyran-4-yl)-1H-isochromen-1-one | HCID 118131261 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178463588 | HCID 178463588 | 5.8% |
Reaction Steps
The title compound was made in a similar way as that of the compound of example 21, from tert-butyl 9-trityl-9H-purin-6-ylcarbamate (214 mg, 0.449 mmol) and 3-(1-bromoethyl)-4-(3,6-dihydro-2H-pyran-4-yl)-1H-isochromen-1-one (intermediate C19, 94 mg, 0.280 mmol) and 50% dispersion in mineral oil NaH (18 mg, 0.34 mmol) in DMF. This was purified via reverse phase chromatography with a Biotage C18 SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%). Fractions containing the required product were collected, 1 M HClaqueous (5 ml) was added and concentrated under reduced pressure to give the title compound (6.3 mg, 5.8%) as colourless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321776B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-788cea912d934b03b29c8ee52bc8b543 |
| Source note | uspto-grants-2016_04 |