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

HRID 9767

Reaction equation

HRID 9767 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 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

2-Amino-thiophene-3-carboxlic acid amide (28.4 g, 0.2 mol) and potassium ethylxanthate (96 g, 3 eq) were mixed together and added to DMF (1000 mL). The resulting mixture was heated to 150° C. for about six hours. The solvent (DMF) was removed on the rotovap under high vacuum at 90° C. The residue was diluted with 600 mL of aqueous citric acid (5%) and cooled to 0° C. and stirred for about 30 minutes. The tan powder was filtered and dried overnight to give 25.6 g of the title compound ((M+H)+=185, M.P.>300° C.).

Workup

  1. customThe solvent (DMF) was removed on the rotovap under high vacuum at 90° C
  2. additionThe residue was diluted with 600 mL of aqueous citric acid (5%)
  3. temperaturecooled to 0° C.
  4. filtrationThe tan powder was filtered
  5. customdried overnight

Sources & evidence

ORD record
ord-9a87187d185b4d9390fcb9daeac9bc76
Source dataset
uspto-grants-2006_08
Patent number
US07091347B2

Linked notes

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