Aluminium lithium hydride → HCID 68313089, compound

HRID 1530489Notes

Reaction equation

HRID 1530489 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](OC)=[O: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]([CH2:23][OH:24])=[CH:15][CH:16]=2)=[N:7][CH:6]=[N:5]1)[CH3:1]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68312674HCID 68312674, compound

Product 1

HCID 68313089HCID 68313089, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 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-pentaene-13-carboxylate (1.70 g, 4.82 mmol) in THF (150 mL) was added LiAlH4 (732 mg, 19.3 mmol). The reaction mixture was heated to reflux for 2 hours. After cooling down, the reaction was quenched with a piece of ice cube at 0° C. The solid was filtered off and washed with ethyl acetate (3×30 mL). The combined filtrate was concentrate to give the crude product, which was purified by column chromatography on silica gel eluting with a 50% gradient of EtOAc in petroleum ether to afford {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}methanol (1.30 g, 83% yield) as a pale yellow solid. LCMS (ESI) m/z: 326.2 [M+H+].

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter cooling down
  4. customthe reaction was quenched with a piece of ice cube at 0° C
  5. filtrationThe solid was filtered off
  6. washwashed with ethyl acetate (3×30 mL)
  7. concentrationThe combined filtrate was concentrate
  8. customto give the crude product, which
  9. customwas purified by column chromatography on silica gel eluting with a 50% gradient of EtOAc in petroleum ether

Sources & evidence

ORD record
ord-50f661cc0785415cb8e509104318cd10
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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