Aluminium lithium hydride → HCID 178480829, compound

HRID 639386Notes

Reaction equation

HRID 639386 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([C:32]([N:34]5[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]5)=O)=[CH:28][CH:27]=4)[N:20]=3)=[CH:17][NH:16][N:15]=2)=[CH:10][CH:9]=1>C1COCC1.O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]4[CH:27]=[CH:28][C:29]([CH2:32][N:34]5[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]5)=[CH:30][CH:31]=4)[N:20]=3)=[CH:17][NH:16][N:15]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178481039HCID 178481039, compound

Product 1

HCID 178480829HCID 178480829, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To the suspension of 96 mg (2.53 mMol; 4 Eq.) of lithium aluminum hydride (Fluka 62420) in 20 mL of THF abs. under Argon at rt is added slowly within 10 min 300 mg (0.633 mMol) of (4-{4-([3-(4-chloro-phenyl)-1H-pyrazol-4-yl]-pyrimidin-2-ylamino}-phenyl)-(4-methyl-piperazin-1-yl)-methanone (see Example 31) as a solid; under vigorous foaming. After stirring for 2.5 h at rt, the suspension is cooled to 0° C. and treated dropwise with 20 mL of water. After diluting further with 50 mL of water, the suspension is extracted with ethyl acetate. The combined organic layers are washed with water, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product is purified over silica gel, eluting with CH2Cl2/CH3OH (4:1) followed by trituration in diethyl ether to obtain {4-[3-(4-chloro-phenyl)-1H-pyrazol-4-yl]-pyrimidin-2-yl}-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-amine.

Workup

  1. temperaturethe suspension is cooled to 0° C.
  2. extractionthe suspension is extracted with ethyl acetate
  3. washThe combined organic layers are washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified over silica gel
  8. washeluting with CH2Cl2/CH3OH (4:1)

Sources & evidence

ORD record
ord-2d7b3a118631414293646253c9a5410b
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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