Aluminium lithium hydride → HCID 58688031, compound

HRID 551877Notes

Reaction equation

HRID 551877 reaction equation
[NH2:1][C:2]1[C:3]([CH3:32])=[C:4]([C:8]2[N:9]=[C:10]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=O)=[CH:20][CH:19]=3)[C:11]3[N:12]([CH:14]=[CH:15][N:16]=3)[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:1][C:2]1[C:3]([CH3:32])=[C:4]([C:8]2[N:9]=[C:10]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([CH2:24][N:26]4[CH2:27][CH2:28][O:29][CH2:30][CH2:31]4)=[CH:22][CH:23]=3)[C:11]3[N:12]([CH:14]=[CH:15][N:16]=3)[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58688037HCID 58688037, compound

Product 1

HCID 58688031HCID 58688031, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

{4-[6-(3-Amino-2-methyl-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-phenyl}-morpholin-4-yl-methanone (350 mg; 0.82 mmol) is dissolved in anhydrous THF (5 mL) under nitrogen at rt. Solid lithium aluminum hydride (0.5 g) is added portion-wise to the stirring reaction, and the reaction refluxed under nitrogen for 2 hr. The reaction is cooled to 0° C. in an ice bath and quenched carefully by the dropwise addition of water (0.5 mL), then 15% NaOH(aq) (0.5 mL), and finally by more water (5 mL). The reaction is stirred at 0° C. for 15 minutes then the slurry is filtered through celite to remove the aluminum salts. The filtrate is partitioned between water and ethyl acetate, and the ethyl acetate layer is washed with water (1×50 mL), and brine (1×50 mL), then dried over anhydrous sodium sulfate and concentrated in vacuo to provide [6-(3-amino-2-methyl-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-(4-morpholin-4-ylmethyl-phenyl)-amine as a tan solid (300 mg), which is pure enough to use in further steps.

Workup

  1. customto the stirring reaction
  2. temperaturethe reaction refluxed under nitrogen for 2 hr
  3. customquenched carefully by the dropwise addition of water (0.5 mL)
  4. filtrationthe slurry is filtered through celite
  5. customto remove the aluminum salts
  6. customThe filtrate is partitioned between water and ethyl acetate
  7. washthe ethyl acetate layer is washed with water (1×50 mL), and brine (1×50 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b83070328075427d8b8f83be12d5005a
Source dataset
uspto-grants-2011_05
Patent number
US07947835B2

Reaction notes

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