Aluminium lithium hydride → HCID 11554303, compound

HRID 221902Notes

Reaction equation

HRID 221902 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)=[CH:24][CH:23]=2)=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([N:8]2[C:7]([NH:18][C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]4[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=4)=[CH:24][CH:23]=3)=[O:20])=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:9]2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53630191HCID 53630191, compound

Product 1

HCID 11554303HCID 11554303, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-[5-tert-butyl-2-(4-cyano-phenyl)-2H-pyrazol-3-yl]-3-[4-(pyridin-4-yloxy)phenyl]urea (4.0 g, 8.8 mmol) in anhydrous THF (20 mL) was added a solution of lithium aluminum hydride in THF (1M, 9.7 mL, 9.7 mmol) with stirring at 0° C. under nitrogen, and then the reaction mixture was stirred at room temperature for 5 h. The excess lithium aluminum hydride was quenched by dropwise addition of EtOAc (5 mL) followed by EtOH (5 mL) and then 10% aqueous KHSO4 solution (5 mL). The reaction mixture was stirred at room temperature for an additional 10 min, and was then filtered through a pad of Celite® filter agent. The Celite® was washed with EtOH (50 mL) and the filtrate was concentrated at reduced pressure. The residue was purified by MPLC (80:20 CH2Cl2/MeOH) to give 3.2 g (79%) of the desired product. 1H-NMR (DMSO-d6) δ 9.38 (s, 1H), 8.41 (dd, J=1.5, 4.8 Hz, 2H), 7.49 to 7.46 (m, 6H), 7.07 (d, J=6.9 Hz, 2H), 6.85 (dd, J=1.8, 4.8 Hz, 2H), 6.32 (s, 1H), 3.82 (s, 2H), 1.26 (s, 9H); MS LC-MS [M+H]+=457, RT=1.96 min.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 5 h
  2. customThe excess lithium aluminum hydride was quenched by dropwise addition of EtOAc (5 mL)
  3. stirringThe reaction mixture was stirred at room temperature for an additional 10 min
  4. filtrationwas then filtered through a pad of Celite®
  5. filtrationfilter agent
  6. washThe Celite® was washed with EtOH (50 mL)
  7. concentrationthe filtrate was concentrated at reduced pressure
  8. customThe residue was purified by MPLC (80:20 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-aec8e22a35de474e86988ef4c6fda3c5
Source dataset
uspto-grants-2012_06
Patent number
US08207166B2

Reaction notes

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