Cesium carbonate → HCID 123399378, compound

HRID 2174176Notes

Reaction equation

HRID 2174176 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:11][C:10]([C:12](=[N:14][OH:15])[CH3:13])=[N:9][N:8]=2)[CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1>C(#N)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:11][C:10]([C:12](=[N:14][O:15][C:23]3[N:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH3:13])=[N:9][N:8]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 744042-ChloropyrimidineHCID 137231112HCID 137231112, compound

Product 1

HCID 123399378HCID 123399378, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-[5-(3-pyridyl)-1,3,4-thiadiazol-2-yl]ethanone oxime (0.1 g, 0.436 mmol) in acetonitrile (5 ml) was stirred at ambient temperature and treated with cesium carbonate (0.43 g, 1.31 mmol) and 2-chloropyrimidine (0.079 g, 0.654 mmol). The reaction mixture was allowed to stir at ambient temperature and monitored by TLC and LC/MS. After 2 days, the mixture was concentrated in vacuo. The residue was stirred with ethyl acetate, filtered and the ethyl acetate concentrated in vacuo. Purification by recrystallisation gave a single isomer of 1-[5-(3-pyridyl)-1,3,4-thiadiazol-2-yl]-N-pyrimidin-2-yloxy-ethanimine (70 mg, 23%) in form of beige crystals.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. stirringThe residue was stirred with ethyl acetate
  3. filtrationfiltered
  4. concentrationthe ethyl acetate concentrated in vacuo
  5. customPurification
  6. customby recrystallisation

Sources & evidence

ORD record
ord-c867f15094e54228bfaccfec739f942c
Source dataset
uspto-grants-2015_06
Patent number
US09060519B2

Reaction notes

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