4-Ethyl-5-ethynylthiazol-2-amine → 2-Thiazolamine, 4,5-diethyl-

HRID 1009041Notes

Reaction equation

HRID 1009041 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([NH2:10])[S:6][C:7]=1[C:8]#[CH:9])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([C:3]1[N:4]=[C:5]([NH2:10])[S:6][C:7]=1[CH2:8][CH3:9])[CH3:2]

Participants

4

Reactant 1

HCID 866309564-Ethyl-5-ethynylthiazol-2-amine

Product 1

HCID 128317712-Thiazolamine, 4,5-diethyl-Yield 70.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The above prepared 4-ethyl-5-ethynyl-thiazol-2-ylamine (0.255 g, 1.675 mmol) was dissolved in 8 mL of ethyl acetate and hydrogenated over 0.125 g of Pd on charcoal (10%) at atmospheric pressure and ambient temperature over night. Filtration over a pad of Ceite and evaporation off all solvents, followed by flash chromatography (SiO2, hexane/ethyl acetate=6/4), yielded 0.184 g of the title product as light yellow solid.

Workup

  1. filtrationFiltration
  2. customover a pad of Ceite and evaporation off all solvents

Sources & evidence

ORD record
ord-7adc8671c3e04bdc84a4db3d33985a93
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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