Cesium carbonate → HCID 67273555, compound

HRID 1696751Notes

Reaction equation

HRID 1696751 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([NH2:9])[N:6]=[C:5]([NH2:10])[CH:4]=1.[C:11]([Si:15]([O:18][CH2:19][CH2:20]I)([CH3:17])[CH3:16])([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[C:11]([Si:15]([CH3:17])([CH3:16])[O:18][CH2:19][CH2:20][NH:10][C:5]1[CH:4]=[C:3]([S:2][CH3:1])[CH:8]=[C:7]([NH2:9])[N:6]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilaneHCID 672745044-Methylsulfanyl-pyridine-2,6-diamine

Product 1

HCID 67273555HCID 67273555, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a glass vessel were mixed together the above prepared 4-methylsulfanyl-pyridine-2,6-diamine (0.350 g, 2.25 mmol), tert-butyl-(2-iodo-ethoxy)-dimethyl-silane (CAS 101166-65-8, 0.700 g, 1.08 eq.), and 1.2 eq. of Cs2CO3 (0.882 g) in 3.5 mL of abs. acetonitrile, and the mixture allowed to react for 2 h at 125° C. in a microwave oven. Cooling, pouring onto crashed ice, twofold extraction with AcOEt, washing with water and brine, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=4/6) afforded 0.155 g of the title compound as light brown oil.

Workup

  1. additionIn a glass vessel were mixed together the
  2. customto react for 2 h at 125° C. in a microwave oven
  3. temperatureCooling
  4. additionpouring
  5. extractionice, twofold extraction with AcOEt
  6. washwashing with water and brine
  7. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-c4ae1a5242ec4ad880edf42c07071d8a
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

Loading…