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

HRID 564508Notes

Reaction equation

HRID 564508 reaction equation
[NH2:1][CH2:2][C:3]1[C:8]([CH2:9][CH3:10])=[N:7][C:6]2[N:11]([CH2:14][CH3:15])[N:12]=[CH:13][C:5]=2[C:4]=1[NH:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.[CH3:23]C(OC(OC(OC(C)(C)C)=O)=O)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:14]([N:11]1[C:6]2[N:7]=[C:8]([CH2:9][CH3:10])[C:3]([CH2:2][NH:1][CH3:23])=[C:4]([NH:16][CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[C:5]=2[CH:13]=[N:12]1)[CH3:15]

Participants

5

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 21226445Aluminium lithium hydrideHCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

Product 1

HCID 578133271,6-Diethyl-5-[(methylamino)methyl]-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amineYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

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)+.

Workup

  1. additionwas added
  2. customThe reaction was then quenched with Na2SO4 (sat. aq.)
  3. filtrationfiltered
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8aae5223613d47bf9a29f492c93161ed
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

Loading…