Potassium Carbonate → 4-Ethyl-5-ethynylthiazol-2-amine
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
Product 1
Reagents, catalysts & solvents 1
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
- additionPouring
- extractionice/NH4Cl, twofold extraction with ethyl acetate
- washwashing with water and brine
- 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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