HCID 178437084, compound → HCID 178437085, compound

HRID 1019718Notes

Reaction equation

HRID 1019718 reaction equation
[CH:1]([C:3]1[N:8]=[C:7]2[N:9]([C@H:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH3:14])[C:10]([OH:12])=[N:11][C:6]2=[N:5][CH:4]=1)=[CH2:2]>[Pd].CO>[C:15]1([C@@H:13]([N:9]2[C:7]3=[N:8][C:3]([CH2:1][CH3:2])=[CH:4][N:5]=[C:6]3[N:11]=[C:10]2[OH:12])[CH3:14])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 178437084HCID 178437084, compound

Product 1

HCID 178437085HCID 178437085, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A scintillation vial equipped with a stirbar was charged with (S)-6-vinyl-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol (1.0 equiv), methanol (280 volume equivalents), and catalytic Pd/C. The resulting mixture was purged with hydrogen for 45 minutes; the reaction was complete as judged my LCMS. The mixture was then filtered through a pad of diatomaceous earth and the pad of diatomaceous earth was washed twice with MeOH. The solution was concentrated in vacuo. Flash chromatography (Biotage MPLC 5%-40% EtOAc/Hexanes) provided the title compound (86%) as a foam. LCMS m/z (APCI)=269.1 (M+H).

Workup

  1. customA scintillation vial equipped with a stirbar
  2. customThe resulting mixture was purged with hydrogen for 45 minutes
  3. filtrationThe mixture was then filtered through a pad of diatomaceous earth
  4. washthe pad of diatomaceous earth was washed twice with MeOH
  5. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-22fde8ee4a5c4173b33988755433753f
Source dataset
uspto-grants-2014_05
Patent number
US08716291B2

Reaction notes

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