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 657363Notes

Reaction equation

HRID 657363 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

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). 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)+.

Workup

  1. temperaturethat mixture heated with a microwave machine at 100° C. for 30 mins
  2. customThe reaction was then quenched with Na2SO4 (sat. aq.) slowly
  3. filtrationfiltered
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dc1fc89e2af74bffb9c2b6d3f4923661
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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