Carbonate Ion → HCID 123842023, compound

HRID 2174180Notes

Reaction equation

HRID 2174180 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][C:9]([C:12](=[N:14][OH:15])[CH3:13])=[CH:10][N:11]=2)[CH:2]=1.C(=O)([O-])[O-].Cl[C:21]1[N:26]=[CH:25][CH:24]=[CH:23][N:22]=1>C(#N)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][C:9]([C:12](=[N:14][O:15][C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH3:13])=[CH:10][N:11]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 19660Carbonate IonHCID 744042-ChloropyrimidineHCID 131732977HCID 131732977, compound

Product 1

HCID 123842023HCID 123842023, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1-[2-(3-pyridyl)thiazol-5-yl]ethanone oxime (isomer A, 0.15 g, 0.657 mmol) in acetonitrile (5 ml) was stirred at ambient temperature and treated with carbonate (0.648 g, 1.97 mmol) and 2-chloropyrimidine (0.119 g, 0.985 mmol) and allowed to stir at ambient temperature. After 2 days (80% conversion), the reaction mixture was concentrated in vacuo and the residue was stirred with ethyl acetate, filtered and the ethyl acetate concentrated in vacuo. Purification by flash chromatography eluting with ethyl acetate gave 1-[2-(3-pyridyl)thiazol-5-yl]-N-pyrimidin-2-yloxy-ethanimine (0.074 g, 38%) as a single isomer as slightly yellow crystals.

Workup

  1. stirringto stir at ambient temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. stirringthe residue was stirred with ethyl acetate
  4. filtrationfiltered
  5. concentrationthe ethyl acetate concentrated in vacuo
  6. customPurification by flash chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-a3393e8e7d144a17acd4ec2aae4287af
Source dataset
uspto-grants-2015_06
Patent number
US09060519B2

Reaction notes

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