Ethyl 2-amino-4-phenylthiophene-3-carboxylate → Thieno(2,3-d)pyrimidin-4(1H)-one, 5-phenyl-

HRID 910180Notes

Reaction equation

HRID 910180 reaction equation
C([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[NH2:17])=O)C.C(O)(=O)C.[CH:22](N)=[NH:23]>C(O)C>[C:11]1([C:10]2[C:6]3[C:4](=[O:3])[NH:23][CH:22]=[N:17][C:7]=3[S:8][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 73242Ethyl 2-amino-4-phenylthiophene-3-carboxylateHCID 160693Formamidine acetate

Product 1

HCID 215639Thieno(2,3-d)pyrimidin-4(1H)-one, 5-phenyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 2-amino-4-phenylthiophene-3-carboxylic acid ethyl ester (350.43 g, 1.535 mol), formamidine acetate (799.13 g, 7.7 mol) and ethanol (1500 ml) was heated under reflux for 18 hours then allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with a little cold ethanol, then crystallised from ethanol to give 5-Phenyl-3H-thieno[2,3-d]pyrimidin-4-one as a yellow solid which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with a little cold ethanol
  5. customcrystallised from ethanol

Sources & evidence

ORD record
ord-6e912309763f44a5a8a3d8b62049b509
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

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