Potassium Carbonate → HCID 68458843, compound

HRID 2356627Notes

Reaction equation

HRID 2356627 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]([C:19]#[N:20])[N:13]=1)(=O)C>CO>[OH:10][CH2:11][C:12]1[N:13]=[C:14]([C:19]#[N:20])[CH:15]=[CH:16][C:17]=1[CH3:18]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68457478(6-Cyano-3-methyl-2-pyridinyl)methyl acetate

Product 1

HCID 68458843HCID 68458843, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (65 mg) was added to a solution of (6-cyano-3-methyl-2-pyridinyl)methyl acetate (2.89 g) in methanol (20 ml) and the mixture stirred under argon at ambient temperature for 2.5 hours. It was concentrated in vacuo to ca. ½ volume and water (40 ml) added. The mixture was neutralized with 5% acetic acid (1.2 ml) and extracted with dichloromethane (40 ml then 2×20 ml). The combined extracts were washed with brine (20 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by Biotage chromatography eluting with 2:1 hexane:ethyl acetate to afford the title compound (1.45 g, 64%) as a pale buff solid. LC/MS [MH+]=149, RT=1.46 min.

Workup

  1. concentrationIt was concentrated in vacuo to ca. ½ volume and water (40 ml)
  2. additionadded
  3. extractionextracted with dichloromethane (40 ml
  4. washThe combined extracts were washed with brine (20 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by Biotage chromatography
  8. washeluting with 2:1 hexane

Sources & evidence

ORD record
ord-9e0994d735094a519d98eaf2f04cce2b
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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