Aluminium lithium hydride → HCID 59811504, compound

HRID 2113796Notes

Reaction equation

HRID 2113796 reaction equation
C(O[C:6](=O)[NH:7][C:8]1[N:9]([CH3:26])[N:10]=[C:11]2[C:16]=1[CH2:15][CH2:14][CH2:13][N:12]2[C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1[CH3:25])(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:6][NH:7][C:8]1[N:9]([CH3:26])[N:10]=[C:11]2[C:16]=1[CH2:15][CH2:14][CH2:13][N:12]2[C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1[CH3:25]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59811513HCID 59811513, compound

Product 1

HCID 59811504HCID 59811504, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of [2-methyl-7-(2,4,6-trimethyl-phenyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]-carbamic acid tert-butyl ester (0.150 g, 0.40 mmol) dissolved in THF (3 mL) was treated with the slow addition of 1M lithium aluminum hydride in THF (0.80 mL, 0.80 mmol). The mixture was placed under a nitrogen atmosphere and heated to reflux for 8 h. The mixture was cooled to room temperature and the excess reagent was quenched by the dropwise addition of 10% potassium sodium tartrate solution. Ethyl acetate (40 mL) was added and washed sequentially with 10% Rochelle salt solution (40 mL) and brine (25 m), dried over magnesium sulfate, and evaporated. The residue was purified by silica gel chromatography eluting with ethyl acetate/hexane (3:2) to afford 0.056 g (48% yield) of methyl-[2-methyl-7-(2,4,6-trimethyl-phenyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]-amine (5-49): mp 143.3-144.9° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 8 h
  3. customthe excess reagent was quenched by the dropwise addition of 10% potassium sodium tartrate solution
  4. additionEthyl acetate (40 mL) was added
  5. washwashed sequentially with 10% Rochelle salt solution (40 mL) and brine (25 m)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with ethyl acetate/hexane (3:2)

Sources & evidence

ORD record
ord-dc6477f2f36b4cb299236b4de8490abd
Source dataset
uspto-grants-2008_10
Patent number
US07432283B2

Reaction notes

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