Ethyl Acetate → 1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)ethanol

HRID 2204480Notes

Reaction equation

HRID 2204480 reaction equation
C[Mg]Cl.[S:4]([N:14]1[C:18]2=[N:19][CH:20]=[C:21]([CH:23]=[O:24])[N:22]=[C:17]2[CH:16]=[CH:15]1)([C:7]1[CH:13]=[CH:12][C:10]([CH3:11])=[CH:9][CH:8]=1)(=[O:6])=[O:5].[NH4+].[Cl-].[CH3:27]COC(C)=O>C1COCC1.C(Cl)Cl>[S:4]([N:14]1[C:18]2=[N:19][CH:20]=[C:21]([CH:23]([OH:24])[CH3:27])[N:22]=[C:17]2[CH:16]=[CH:15]1)([C:7]1[CH:8]=[CH:9][C:10]([CH3:11])=[CH:12][CH:13]=1)(=[O:5])=[O:6]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 580098835-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehydeHCID 178418332HCID 178418332, compound

Product 1

HCID 580102001-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)ethanolYield 23%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methylmagnesium chloride (0.232 mL, 0.697 mmol) in THF (10 mL) at about −78° C. was added a solution of 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde (0.210 g, 0.697 mmol, Example #10, Step B) in DCM (10.0 mL). After about 10 min saturated aqueous NH4Cl was added to the reaction mixture. After warming to room temperature, EtOAc (30 mL) was added to the reaction mixture and the organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 20-80% EtOAc/heptane to provide 1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)ethanol (0.050 g, 23%) as a yellow oil. LC/MS (Table 2, Method a) Rt=2.04 min; MS m/z: 318 (M+H)+.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by silica gel chromatography
  6. washeluting with 20-80% EtOAc/heptane

Sources & evidence

ORD record
ord-c85c60a22d764796851d294ce2b69573
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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