Aluminium lithium hydride → HCID 57833392, compound

HRID 2244167Notes

Reaction equation

HRID 2244167 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:28]=[CH:27][C:12]([O:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]([NH:22][CH2:23][CH2:24][O:25][CH3:26])=O)[CH:15]=3)=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H][H]>C1COCC1>[CH3:26][O:25][CH2:24][CH2:23][NH:22][CH2:20][C:16]1[CH:15]=[C:14]([O:13][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6]3[CH:5]=[C:4]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:3]=[C:2]([NH2:1])[N:7]=3)=[CH:28][CH:27]=2)[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 57833236HCID 57833236, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57833392HCID 57833392, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-{4-[(2-amino-6-phenylpyrimidin-4-yl) amino]phenoxy}-N-(2-methoxyethyl)pyridine-2-carboxamide from Example 23 (50 mmol) in anhydrous THF (50 mL) is added in portions to a pre-cooled in ice-bath solution of lithium aluminum hydride (100 mmol, 1.0 M in THF) in anhydrous THF (150 mL). The reaction is stirred at 0° C. for 30 min until evolution of hydrogen subsides. The reaction mixture is refluxed under nitrogen for 48 h. The mixture is brought to 5-10° C. and carefully quenched with water (3.8 mL), 15% NaOH (3.8 mL) and water (12 ruL). The mixture is extracted with EtOAc and the organic layer is dried and concentrated to give a crude product which is purified by chromatography on a silica column to give the title compound.

Workup

  1. temperatureThe reaction mixture is refluxed under nitrogen for 48 h
  2. customis brought to 5-10° C.
  3. customcarefully quenched with water (3.8 mL), 15% NaOH (3.8 mL) and water (12 ruL)
  4. extractionThe mixture is extracted with EtOAc
  5. customthe organic layer is dried
  6. concentrationconcentrated
  7. customto give a crude product which
  8. customis purified by chromatography on a silica column

Sources & evidence

ORD record
ord-373973bb2ba042f89d2d8c33baea98c7
Source dataset
uspto-grants-2010_03
Patent number
US07678804B2

Reaction notes

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