Potassium Carbonate → 4-Ethyl-5-ethynylthiazol-2-amine

HRID 1009040Notes

Reaction equation

HRID 1009040 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([NH2:14])[S:6][C:7]=1[C:8]#[C:9][Si](C)(C)C)[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO>[CH2:1]([C:3]1[N:4]=[C:5]([NH2:14])[S:6][C:7]=1[C:8]#[CH:9])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 866309554-Ethyl-5-trimethylsilanylethynyl-thiazol-2-ylamine

Product 1

HCID 866309564-Ethyl-5-ethynylthiazol-2-amineYield 63.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the above prepared 4-ethyl-5-trimethylsilanylethynyl-thiazol-2-ylamine (0.595 g, 2.651 mmol), dissolved in 9 mL of MeOH, was added K2CO3 (0.550 g, 1.5 eq.) and the mixture was stirred for 2 h at ambient temperature. Pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate, washing with water and brine, drying over sodium sulfate, and evaporation to dryness, followed by flash chromatography (SiO2, hexane/ethyl acetate=7/3), produced 0.256 g of the title compound as light brown solid.

Workup

  1. additionPouring
  2. extractionice/NH4Cl, twofold extraction with ethyl acetate
  3. washwashing with water and brine
  4. dry with materialdrying over sodium sulfate, and evaporation to dryness

Sources & evidence

ORD record
ord-5843305d78d04e98a58054c35375793c
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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