Cesium carbonate → HCID 123842023, compound

HRID 2174181Notes

Reaction equation

HRID 2174181 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][C:9]([C:12](=[N:14]O)[CH3:13])=[CH:10][N:11]=2)[CH:2]=1.[C:16](=[O:19])([O-])[O-].[Cs+].[Cs+]>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:19][C:16]3[N:11]=[CH:7][CH:3]=[CH:2][N:1]=3)[CH3:13])=[CH:10][N:11]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 131732977HCID 131732977, compound

Product 1

HCID 123842023HCID 123842023, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1-[2-(3-pyridyl)thiazol-5-yl]ethanone oxime (76 mg, 0.33 mmol) and cesium carbonate (330 mg, 1.0 mmol) in acetonitrile (10 ml) was stirred at ambient temperature and treated with 2-chlopyrimidine (60 mg, 0.5 mmol). The reaction was monitored by TLC and LC/MS until ca. 70% completion, and then concentrated in vacuo. The solid residue was stirred with ethyl acetate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography, eluting with ethyl acetate:MeOH (95:5), to give isomer B of 1-[2-(3-pyridyl)thiazol-5-yl]-N-pyrimidin-2-yloxy-ethanimine (46 mg, 46%) as white crystals.

Workup

  1. additiontreated with 2-chlopyrimidine (60 mg, 0.5 mmol)
  2. concentrationconcentrated in vacuo
  3. stirringThe solid residue was stirred with ethyl acetate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography
  7. washeluting with ethyl acetate:MeOH (95:5)

Sources & evidence

ORD record
ord-67dba236f5dc46598edf029b5c821f75
Source dataset
uspto-grants-2015_06
Patent number
US09060519B2

Reaction notes

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