HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-(4-chloro-6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-5-yl}ethanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Aminoindane, (S)- | HCID 7000084 | — |
| Reactant | 2-(4,6-Dichloropyrimidin-5-yl)ethan-1-ol | HCID 52988146 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Product | 2-(4-chloro-6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-5-yl}ethanol | HCID 59671318 | 98.2% |
Reaction Conditions
| Temperature | 130 °C |
|---|
Reaction Steps
2-(4,6-dichloropyrimidin-5-yl)ethanol (1.90 g, 9.84 mmol) was dissolved in 1-butanol (97 mL) and N,N-Diisopropylethylamine (3.43 mL, 19.7 mmol) and (S)-1-Aminoindane (1.26 mL, 9.84 mmol) were added. The solution was heated at 130° C. for 3 days. Solvent was removed in vacuo and the residue was purified using chromatography on silica gel using gradient 0 to 100% ethyl acetate in methylene chloride to afford the title compound (2.80 g, 98%). LC/MS: Rt=1.63 min, ES+ 290 (AA standard).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150525B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-245f6dd959f54050a9051d77983cff0c |
| Source note | uspto-grants-2015_10 |