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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 564508Generated: October 30, 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/564508

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 Conditions

Temperature100 °C

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) with stirring at room temperature for 30 min whereupon LAH (5.0 mL, 1.0 M in THF) was added and the mixture heated with a microwave at 100° C. for 30 min. The reaction was then quenched with Na2SO4 (sat. aq.), filtered, dried over Na2SO4, filtered, concentrated to afford the title compound 0.252 g (79%). LC-MS m/z 318 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08067408B2
Source datasetuspto-grants-2011_11
ORD IDord-8aae5223613d47bf9a29f492c93161ed
Source noteuspto-grants-2011_11