Hydrochloric Acid → {6-[(1-tert-Butyl-1H-pyrazol-5-yl)amino]pyrazin-2-yl}methanol

HRID 605591Notes

Reaction equation

HRID 605591 reaction equation
[C:1]([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH:17]=[O:18])[CH:14]=[N:13][CH:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].Cl>C(O)C>[C:1]([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][OH:18])[CH:14]=[N:13][CH:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59152181HCID 59152181, compound

Product 1

HCID 59152207{6-[(1-tert-Butyl-1H-pyrazol-5-yl)amino]pyrazin-2-yl}methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 14.99 g of 6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyrazin-2-carbaldehyde in 235 ml of ethanol was added 2.31 g of sodium borohydride under cooling with ice, followed by stirring the reaction mixture for 1 hour. After slowly adding 61 ml of 1M hydrochloric acid to the reaction mixture under cooling with ice, ethanol was concentrated in vacuo. The obtained residue was diluted with water, and extracted with chloroform. The resulting chloroform solution was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The obtained residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=20/1) to give the title compound as a brown solid.

Workup

  1. temperatureunder cooling with ice
  2. concentrationwas concentrated in vacuo
  3. additionThe obtained residue was diluted with water
  4. extractionextracted with chloroform
  5. washThe resulting chloroform solution was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customThe obtained residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-8527d7e2d2c84039b42cf3e7ac7e066f
Source dataset
uspto-grants-2011_03
Patent number
US07915263B2

Reaction notes

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