Ethyl 2-amino-4-phenylthiophene-3-carboxylate → HCID 67382085, compound

HRID 928593Notes

Reaction equation

HRID 928593 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]=1[C:7]([O:9]CC)=O.[F:18][C:19]([F:24])([F:23])[C:20](N)=[NH:21]>C(O)C>[C:12]1([C:5]2[C:6]3[C:7](=[O:9])[NH:21][C:20]([C:19]([F:24])([F:23])[F:18])=[N:1][C:2]=3[S:3][CH:4]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 73242Ethyl 2-amino-4-phenylthiophene-3-carboxylateHCID 2776882Trifluoroacetamidine2×

Product 1

HCID 67382085HCID 67382085, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-amino-4-phenyl-thiophene-3-carboxylate (2 g, 8.087 mmol) and trifluoroacetamidine (4.531 g, 40.44 mmol) were combined in ethanol (20 mL) and heated to reflux overnight. Further trifluoroacetamidine (4.531 g, 40.44 mmol) was added and the reaction heated to reflux for a further 18 hours. The reaction mixture was allowed to cool to room temperature. The resulting precipitate was filtered off, washed with ethanol (5 mL) and dried in vacuo at 40° C. to afford 5-phenyl-2-(trifluoromethyl)-3H-thieno[2,3-d]pyrimidin-4-one (1.195 g). LCMS: purity 99%, RT=4.11 min, M+1=297.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperaturethe reaction heated
  4. temperatureto reflux for a further 18 hours
  5. filtrationThe resulting precipitate was filtered off
  6. washwashed with ethanol (5 mL)
  7. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-635d39ab66754a58aac72a2ce5a53af1
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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