Potassium Fluoride → HCID 178437083, compound

HRID 1817046Notes

Reaction equation

HRID 1817046 reaction equation
[CH3:1][CH2:2][CH:3]([N:6]1[C:10]2=[N:11][C:12]([C:15]#[C:16][Si](C)(C)C)=[CH:13][N:14]=[C:9]2[N:8]=[C:7]1[OH:21])[CH2:4][CH3:5].[F-].[K+]>CO.C1COCC1.O>[C:15]([C:12]1[N:11]=[C:10]2[N:6]([CH:3]([CH2:4][CH3:5])[CH2:2][CH3:1])[C:7]([OH:21])=[N:8][C:9]2=[N:14][CH:13]=1)#[CH:16]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 178446211HCID 178446211, compound

Product 1

HCID 178437083HCID 178437083, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of 1-(pentan-3-yl)-6-((trimethylsilyl)ethynyl)-1H-imidazo[4,5-b]pyrazin-2-ol (3.2 g, 10.6 mmol), KF (1.6 g, 27.5 mmol) in MeOH/THF/H2O (50 mL, 2/2/1) was stirred at room temperature. Upon complete conversion by LCMS, the solution was concentrated in vacuo, diluted with EtOAc, washed with NH4Cl solution, dried over Na2SO4, and concentrated in vacuo. Purification over silica gel (Biotage MPLC 10-80% EtOAc/Hexanes) gave a brown solid, which was washed with 15% EtOAc/hexanes to give product the title compound as a white solid (0.9 g, 37%).

Workup

  1. concentrationUpon complete conversion by LCMS, the solution was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. washwashed with NH4Cl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification over silica gel (Biotage MPLC 10-80% EtOAc/Hexanes)
  7. customgave a brown solid, which
  8. washwas washed with 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-4ced6f6f7cb94e719ddfbcaf3858be7c
Source dataset
uspto-grants-2009_10
Patent number
US07598248B2

Reaction notes

Loading…