Aminopyrazine → Ethyl [(pyrazin-2-yl)carbamothioyl]carbamate

HRID 1411971Notes

Reaction equation

HRID 1411971 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH2:7].[C:8]([N:13]=[C:14]=[S:15])(=[O:12])[O:9][CH2:10][CH3:11]>O1CCOCC1>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:14]([NH:13][C:8](=[O:12])[O:9][CH2:10][CH3:11])=[S:15]

Participants

4

Reactant 2

HCID 78747AminopyrazineHCID 85320Ethyl isothiocyanatoformate

Product 1

HCID 15619487Ethyl [(pyrazin-2-yl)carbamothioyl]carbamateYield 77.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with pyrazin-2-amine (7.6 g, 80.0 mmol, 1.0 eq.), O-ethyl carbonisothiocyanatidate (12.5 g, 95.4 mmol, 1.2 eq.), and dioxane (150 mL). The reaction mixture was stirred at room temperature for 24 hours. After the reaction was complete, it was concentrated to a volume of around 20 mL under reduced pressure and the resulting suspension was filtered. The solid was collected and washed with ethyl acetate (3×20 mL) to afford 270a (14.0 g, 77%) as a white solid. MS-ESI: [M+H]+ 227.3

Workup

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. concentrationit was concentrated to a volume of around 20 mL under reduced pressure
  3. filtrationthe resulting suspension was filtered
  4. customThe solid was collected
  5. washwashed with ethyl acetate (3×20 mL)

Sources & evidence

ORD record
ord-e73f55f82cab4f7daef1bdd955956386
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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