HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-((R)-1-hydroxy-3-methylbutan-2-ylamino)-4-(5-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | D-Valinol | HCID 6950587 | — |
| Reactant | 4-(5-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(methylsulfonyl)pyrimidine-5-carbonitrile | HCID 59414377 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-((R)-1-hydroxy-3-methylbutan-2-ylamino)-4-(5-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile | HCID 59414547 | 77% |
Reaction Steps
A mixture of 4-(5-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(methylsulfonyl)pyrimidine-5-carbonitrile (120 mg, 0.257 mmol), (R)-(−)-2-amino-3-methyl-1-butanol (57 μl, 0.515 mmol) and diisopropylethylamine (90 μl, 0.515 mmol) in THF (4 mL) was heated at reflux for 1 hour. The reaction mixture was concentrated in vacuo and the residue was purified on silica gel by flash column chromatography to give the title compound as a colourless glassy solid (97 mg, 77% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08530489B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-7a32820803b64d7187b823db5dcd807c |
| Source note | uspto-grants-2013_09 |