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

HRID 2260537Notes

Reaction equation

HRID 2260537 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-3e6ed5e5069d4375bd75cb21bf9fd5e9
Source dataset
uspto-grants-1995_12
Patent number
US05478827

Reaction notes

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