Aluminium lithium hydride → HCID 68312910, compound

HRID 1530537Notes

Reaction equation

HRID 1530537 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[N:21]([CH:22]=2)[CH2:20][CH2:19][O:18][C:17]2[C:12]3=[CH:13][C:14]([C:23](=[O:25])[CH3:24])=[CH:15][CH:16]=2)=[N:7][CH:6]=[N:5]1)[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:3][CH:2]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[N:21]([CH:22]=2)[CH2:20][CH2:19][O:18][C:17]2[C:12]3=[CH:13][C:14]([CH:23]([OH:25])[CH3:24])=[CH:15][CH:16]=2)=[N:7][CH:6]=[N:5]1)[CH3:1]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68313073HCID 68313073, compound

Product 1

HCID 68312910HCID 68312910, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-{4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-13-yl}ethan-1-one (500 mg, 1.48 mmol) in THF (50 mL) was added LiAlH4 (0.282 g, 7.37 mmol), then the mixture was heated at 60° C. for 1 h. After cooling to room temperature, the reaction was quenched with a piece of ice cube. The solid was filtered off and washed with ethyl acetate (3×10 mL). The combined filtrate was concentrated to give the crude product, which was purified by silica gel chromatography eluting with DCM/MeOH (50:1) to give 1-{4-[1-(Propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-13-yl}ethan-1-ol (420 mg, 83% yield) as a white solid. LCMS (ESI) m/z: 340.3 [M+H+].

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was quenched with a piece of ice cube
  3. filtrationThe solid was filtered off
  4. washwashed with ethyl acetate (3×10 mL)
  5. concentrationThe combined filtrate was concentrated
  6. customto give the crude product, which
  7. customwas purified by silica gel chromatography
  8. washeluting with DCM/MeOH (50:1)

Sources & evidence

ORD record
ord-ddbb4099691e41dfb7b1e9f75822631b
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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