HuagongsheHuagongshe Chemistry Print Report · For research reference only
Di-tert-butyl dicarbonate → 1,6-Diethyl-5-[(methylamino)methyl]-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Di-tert-butyl dicarbonate | HCID 90495 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | 5-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine | HCID 59683214 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1,6-Diethyl-5-[(methylamino)methyl]-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine | HCID 57813327 | 79.4% |
Reaction Steps
To the solution of 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-amine (0.303 g, 1.0 mmol) in THF (1 mL) was added Boc2O (0.229 g, 1.05 mmol). This mixture was stirred at room temperature for 30 mins and then LAH (5.0 mL, 1.0 M in THF) was added, and that mixture heated with a microwave machine at 100° C. for 30 mins. The reaction was then quenched with Na2SO4 (sat. aq.) slowly, filtered, dried over Na2SO4, filtered, and concentrated to afford 0.252 g (79%) of the title compound. LC-MS m/z 318 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08071588B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-dc1fc89e2af74bffb9c2b6d3f4923661 |
| Source note | uspto-grants-2011_12 |