Aluminium lithium hydride → HCID 67168067, compound

HRID 1517571Notes

Reaction equation

HRID 1517571 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[C:6]([N:11]2[CH:15]=[C:14]([C:16](OCC)=[O:17])[C:13]([CH3:21])=[N:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:3][N:2]([CH2:4][C:5]1[C:6]([N:11]2[CH:15]=[C:14]([CH2:16][OH:17])[C:13]([CH3:21])=[N:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)[CH3:1]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67167880HCID 67167880, compound

Product 1

HCID 67168067HCID 67168067, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 1-[3-(dimethylaminomethyl)-2-pyridyl]-3-methyl-pyrazole-4-carboxylate (217.7 g, 0.75 mmol) in tetrahydrofuran (5 mL) cooled to 0° C. and under nitrogen, 1 M lithium aluminum hydride in tetrahydrofuran (0.9 mL, 0.9 mmol) is added and the mixture is stirred at that temperature for 5 minutes. The reaction is quenched with saturated aqueous solution of ammonium chloride and the crude is extracted with ethyl acetate. The organic layer is separated, dried on sodium sulfate and the solvent is evaporated in vacuo. In this particular example the compound is not isolated in the organic extraction and is finally separated from the aqueous solution with an SCX cartridge to afford 146 mg (78%) of [1-[3-(dimethylaminomethyl)-2-pyridyl]-3-methyl-pyrazol-4-yl]methanol that is used with no further purification. MS (m/z): 247 (M+1).

Workup

  1. customThe reaction is quenched with saturated aqueous solution of ammonium chloride
  2. extractionthe crude is extracted with ethyl acetate
  3. customThe organic layer is separated
  4. customdried on sodium sulfate
  5. customthe solvent is evaporated in vacuo
  6. customis finally separated from the aqueous solution with an SCX cartridge

Sources & evidence

ORD record
ord-e08b63eeec704ccb97401c8c44b3df36
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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