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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 657363Generated: October 29, 2026

Di-tert-butyl dicarbonate → 1,6-Diethyl-5-[(methylamino)methyl]-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

https://huagongshe.com/reaction/657363

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDi-tert-butyl dicarbonateHCID 90495—
ReactantAluminium lithium hydrideHCID 21226445—
Reactant5-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amineHCID 59683214—
SolventTetrahydrofuranHCID 8028—
Product1,6-Diethyl-5-[(methylamino)methyl]-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amineHCID 5781332779.4%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08071588B2
Source datasetuspto-grants-2011_12
ORD IDord-dc1fc89e2af74bffb9c2b6d3f4923661
Source noteuspto-grants-2011_12