Potassium Carbonate → HCID 18779747, compound

HRID 1421692Notes

Reaction equation

HRID 1421692 reaction equation
[CH3:1][C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][N:7]=1.I[C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>[Cu].CCOC(C)=O>[OH:15][CH2:14][C:13]1[CH:16]=[CH:17][C:10]([N:4]2[CH:5]=[CH:6][N:7]=[C:2]([CH3:1])[C:3]2=[O:8])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 290124-Iodobenzyl alcoholHCID 178432940HCID 178432940, compound

Product 1

HCID 18779747HCID 18779747, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-Methyl-2-hydroxypyrazine (1.10 g, 10.0 mmol), 4-Iodobenzyl alcohol from Example 1, Step 1 (4.0 g, 17.0 mmol), K2CO3 (1.52 g, 110 mmol), and copper (15 mg , 0.2 mmol) were heated under argon for 40 hours. The dark residue was partitioned between CHCl3 and saturated NaHCO3. The aqueous layer was back extracted twice with CHCl13. The organic layers were combined, washed with brine, dried (MgSO4,), filtered and concentrated to give a light brown solid. Flash chromatography (EtOAc) yielded the title compound as a yellow solid.

Workup

  1. customThe dark residue was partitioned between CHCl3 and saturated NaHCO3
  2. extractionThe aqueous layer was back extracted twice with CHCl13
  3. washwashed with brine
  4. dry with materialdried (MgSO4,)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a light brown solid

Sources & evidence

ORD record
ord-98a28d97ca644d5493394e88853fb875
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

Loading…