Ethylene Glycol → HCID 57830990, compound

HRID 1642076Notes

Reaction equation

HRID 1642076 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH2:17](O)[CH2:18][OH:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([C:11]3([C:12]([CH3:13])([CH3:15])[CH3:14])[O:19][CH2:18][CH2:17][O:16]3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 25517Ammonium ChlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 578292181-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

Product 1

HCID 57830990HCID 57830990, compoundYield 83.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one (1.5 g, 5.3 mmol) was partly dissolved in 18 ml toluene, and ethylene glycol (0.9 ml, 15.9 mmol) and then p-toluenesulfonic acid hydrate were added. The mixture was refluxed with a Dean-Stark-type trap attached for 24 hr. The reaction was cooled to room temperature and ammonium chloride solution, water and ethyl acetate were added. The layers were separated and the aqueous layer was extracted twice more with ethyl acetate. The combined ethyl acetate layers were washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration and evaporation the residue was purified by silica gel chromatography(ethyl acetate/hexanes to give 1.44 g (83%) of 2-bromo-7-(2-tert-butyl-[1,3]dioxolan-2-yl)-5H-pyrrolo[2,3-b]pyrazine.

Workup

  1. temperatureThe mixture was refluxed with a Dean-Stark-type trap
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice more with ethyl acetate
  4. washThe combined ethyl acetate layers were washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and evaporation the residue
  7. customwas purified by silica gel chromatography(ethyl acetate/hexanes

Sources & evidence

ORD record
ord-bb861b5595a441f2ba2c46d7a1e88c6a
Source dataset
uspto-grants-2012_02
Patent number
US08119636B2

Reaction notes

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