Lithium borohydride → HCID 135974149, compound

HRID 54961Notes

Reaction equation

HRID 54961 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[N:13]=[C:14]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:15]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:9]2[NH:8][CH:7]=1)=[O:5])[CH3:2].[BH4-].[Li+]>O1CCCC1>[CH2:1]([O:3][C:4]([CH:6]1[C:11](=[O:12])[N:10]2[N:13]=[C:14]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[C:15]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:9]2[NH:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 178469871HCID 178469871, compound

Product 1

HCID 135974149HCID 135974149, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4,7-dihydro-6-ethoxycarbonyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)-7-oxopyrazolo[1,5-a]pyrimidine (100 mg) in tetrahydrofuran (4 ml) was added lithium borohydride (2 mole in tetrahydrofuran, 0.26 ml) at room temperature and the mixture was refluxed for 1 hour. After cooling, the reaction mixture was quenched with an aqueous saturated ammonium chloride solution and extracted with ethyl acetate. The extracts were washed with brine, dried and concentrated in vacuo. The residue was crystallized from ethanol to give 6-ethoxycarbonyl-2-(4-fluorophenyl)-7-oxo-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (40 mg).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. customthe reaction mixture was quenched with an aqueous saturated ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-e4e18157eb9541c580754e8c4895a5e7
Source dataset
uspto-grants-1997_04
Patent number
US05624931

Reaction notes

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