2-Mercaptoethanol → 2-(5-Aminopyrazin-2-ylthio)ethanol

HRID 1844536Notes

Reaction equation

HRID 1844536 reaction equation
[OH:1][CH2:2][CH2:3][SH:4].[NH2:5][C:6]1[CH:11]=[N:10][C:9](Br)=[CH:8][N:7]=1>CN(C)C=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:5][C:6]1[N:7]=[CH:8][C:9]([S:4][CH2:3][CH2:2][OH:1])=[N:10][CH:11]=1

Participants

6

Reactant 2

HCID 15672-MercaptoethanolHCID 5995392-Amino-5-bromopyrazine

Product 1

HCID 583285082-(5-Aminopyrazin-2-ylthio)ethanol

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

According to the method described in WO2004/052869, 2-hydroxy-1-ethanethiol (0.93 mL) and tetrakis(triphenylphosphine)palladium (3.39 g) were added to a solution of 2-amino-5-bromopyrazine (1.00 g, 5.75 mmol) in N,N-dimethylformamide (15.1 mL), and the mixture was heated and stirred at 120° C. in a sealed tube for about 3 hours. After cooling, the reaction mixture was diluted with water and extracted with a mixed solution (dichloromethane:ethanol=5:1) (100 mL×6). The organic layer was dried over anhydrous sodium sulfate and then filtrated, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (hexane:ethyl acetate=1:1, then ethyl acetate, and then ethyl acetate:methanol=10:1) and was recrystallized (using chloroform) to give the title compound as yellow needle crystals (470 mg, yield: 44%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. extractionextracted with a mixed solution (dichloromethane:ethanol=5:1) (100 mL×6)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltrated
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography (hexane
  8. customethyl acetate=1:1, then ethyl acetate, and then ethyl acetate:methanol=10:1) and was recrystallized (using chloroform)

Sources & evidence

ORD record
ord-b8154f6b268e4be0b2b414e1ed6870bb
Source dataset
uspto-grants-2015_02
Patent number
US08946440B2

Reaction notes

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