2-Aminothiophene-3-carboxamide → 2-sulfanyl-3H,4H-thieno(2,3-d)pyrimidin-4-one

HRID 19568

Reaction equation

HRID 19568 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].C(O[C:13]([S-])=[S:14])C.[K+]>CN(C=O)C>[S:14]=[C:13]1[NH:1][C:2]2[S:3][CH:4]=[CH:5][C:6]=2[C:7](=[O:8])[NH:9]1

Participants

4

Reactant 2

HCID 6994952-Aminothiophene-3-carboxamideHCID 2735045Potassium ethylxanthate

Product 1

HCID 36033932-sulfanyl-3H,4H-thieno(2,3-d)pyrimidin-4-oneYield 67.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

2-Aminothiophene-3-carboxamide (13 g, 92 mmol) and potassium ethylxanthate (48 g, 275 mmol) were mixed together and added to DMF (300 mL). The resulting mixture was heated to 150° C. for 6 hrs, then cooled to RT and concentrated on the rotovap under reduced pressure at 90° C. The residue was diluted with 300 mL of aqueous citric acid (5%) and cooled to 0° C. and stirred for 30 min. The tan powder was filtered and dried overnight to give (11.5 g) of the title compound MS (ES+): 185 (M+H)+.

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated on the rotovap under reduced pressure at 90° C
  3. additionThe residue was diluted with 300 mL of aqueous citric acid (5%)
  4. temperaturecooled to 0° C.
  5. filtrationThe tan powder was filtered
  6. customdried overnight

Sources & evidence

ORD record
ord-5d20b758be07431cab5abca7aaf31268
Source dataset
uspto-grants-2010_06
Patent number
US07745449B2

Linked notes

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