Sodium borohydride → 1,4-Dihydro-8-(4-fluorophenyl)-4-methyl-7-(pyridin-4-yl)pyrazolo[5,1-c][1,2,4]triazine

HRID 1708026Notes

Reaction equation

HRID 1708026 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[N:10][N:11]3[C:16]([CH3:17])=[CH:15][N:14]=[N:13][C:12]=23)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:18]3[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=3)=[N:10][N:11]3[CH:16]([CH3:17])[CH:15]=[N:14][NH:13][C:12]=23)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 229090688-(4-Fluorophenyl)-4-methyl-7-(pyridin-4-yl)pyrazolo[5,1-c][1,2,4]triazine

Product 1

HCID 1363784171,4-Dihydro-8-(4-fluorophenyl)-4-methyl-7-(pyridin-4-yl)pyrazolo[5,1-c][1,2,4]triazineYield 24.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8-(4-fluorophenyl)-4-methyl-7-(pyridin-4-yl)pyrazolo[5,1-c][1,2,4]triazine (53 mg) and sodium borohydride (13 mg) in ethanol (1 ml) was refluxed for 3 hours, cooled and poured into ice-water. The separated oil was extracted with dichloromethane. The extract was washed with brine, dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from diisopropyl ether to give 1,4-dihydro-8-(4-fluorophenyl)-4-methyl-7-(pyridin-4-yl)pyrazolo[5,1-c][1,2,4]triazine (13 mg).

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperaturecooled
  3. extractionThe separated oil was extracted with dichloromethane
  4. washThe extract was washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel
  8. customthe obtained oil was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-fac2d2cfbdf642eab325c8d7149a4796
Source dataset
uspto-grants-1994_10
Patent number
US05356897

Reaction notes

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