Sodium borohydride → HCID 59570676, compound

HRID 1961713Notes

Reaction equation

HRID 1961713 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]([CH:24]=[O:25])=[N:13][CH:14]=[C:15]([N:17]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[N:18]3)[N:16]=2)=[CH:6][CH:5]=1>CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]2[C:12]([CH2:24][OH:25])=[N:13][CH:14]=[C:15]([N:17]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[N:18]3)[N:16]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59570680HCID 59570680, compound

Product 1

HCID 59570676HCID 59570676, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (25 mg, 0.66 mmol) was added to an ice cooled solution of 3-(4-chloro-phenylamino)-5-(3,5-dimethyl-pyrazol-1-yl) -pyrazine-2-carbaldehyde (80 mg, 0.22 mmol) in methanol (5 mL) and stirred at room temperature for 30 minutes. The reaction was quenched with aqueous sodium hydrogen carbonate and diluted with ethyl acetate. The organic solvents were evaporated and the remaining aqueous phase was extracted with ethyl acetate (3×20 mL). The combined organic phases were washed with brine, dried over sodium sulphate, filtrated and evaporated to give [3-(4-chloro-phenylamino)-5-(3,5-dimethyl-pyrazol-1-yl)-pyrazin-2-yl]-methanol (58 mg, 80%) as the crude product.

Workup

  1. customThe reaction was quenched with aqueous sodium hydrogen carbonate
  2. additiondiluted with ethyl acetate
  3. customThe organic solvents were evaporated
  4. extractionthe remaining aqueous phase was extracted with ethyl acetate (3×20 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltrated
  8. customevaporated

Sources & evidence

ORD record
ord-891c8013effa4b8ea80a01b58cb22095
Source dataset
uspto-grants-2013_04
Patent number
US08415358B2

Reaction notes

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