Triethylamine → HCID 178446211, compound

HRID 1019723Notes

Reaction equation

HRID 1019723 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[C:9]([OH:11])=[N:10][C:5]2=[N:4][CH:3]=1.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19].C(N(CC)CC)C>CN(C=O)C.[Cu]I>[CH3:14][CH2:13][CH:12]([N:8]1[C:6]2=[N:7][C:2]([C:22]#[C:21][Si:18]([CH3:20])([CH3:19])[CH3:17])=[CH:3][N:4]=[C:5]2[N:10]=[C:9]1[OH:11])[CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 178446210HCID 178446210, compound

Product 1

HCID 178446211HCID 178446211, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-bromo-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyrazin-2-ol (3.75 g, 13.2 mmol)), trimethylsilylacetylene (2.8 mL, 19.8 mmol), PdCl2(PPh)2 (0.93 g, 1.32 mmol), CuI (0.5 g, 2.64 mmol) and triethylamine (5.5 mL, 39.5 mmol) in DMF (50 mL) was purged with N2 for 30 seconds followed by stirring at 80° C. After 3 hours the reaction mixture was diluted with EtOAc, washed with NH4Cl solution, dried over Na2SO4, and concentrated in vacuo. Purification with over silica gel (Biotage MPLC 10-80% EtOAc/hexanes) provided the title compound (3.2 g, 80%) as a brown solid.

Workup

  1. customwas purged with N2 for 30 seconds
  2. additionAfter 3 hours the reaction mixture was diluted with EtOAc
  3. washwashed with NH4Cl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification with over silica gel (Biotage MPLC 10-80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-127ee5e209d3444d9e46a9fdd712b31c
Source dataset
uspto-grants-2014_05
Patent number
US08716291B2

Reaction notes

Loading…