Sodium Hydroxide → HCID 58382111, compound

HRID 1628029Notes

Reaction equation

HRID 1628029 reaction equation
S([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[N:19]=[C:14]2[CH:13]=[CH:12]1)(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+]>O1CCOCC1.O>[N:19]1[C:18]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:17][N:16]=[C:15]2[NH:11][CH:12]=[CH:13][C:14]=12

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58382342HCID 58382342, compound

Product 1

HCID 58382111HCID 58382111, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

tert-Butyl (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methylcarbamate (5.08 g, 12.6 mmol) in a mixture of 1,4-dioxane (40 mL) and water (10 mL) was treated with NaOH (2.02 g, 50.5 mmol) then heated to about 85° C. for about 75 min. The mixture was cooled to rt then most of the solvent was removed under reduced pressure. The mixture was diluted with water (25 mL) then DCM (25 mL) and EtOAc (50 mL) were added. The layers were separated then the aqueous layer was extracted with EtOAc (2×25 mL). The combined organics were washed with brine (15 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give tert-butyl (5H-pyrrolo[2,3-b]pyrazin-2-yl)methylcarbamate (2.45 g, 78%): LC/MS (Table 2, Method b) Rt=1.75 min; MS m/z 249 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. custommost of the solvent was removed under reduced pressure
  3. additionThe mixture was diluted with water (25 mL)
  4. additionDCM (25 mL) and EtOAc (50 mL) were added
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc (2×25 mL)
  7. washThe combined organics were washed with brine (15 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e4bafff98ded4070900b23b9055477e2
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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