Ammonia → 2-(3-methoxy-phenyl)-3H-thieno[3,2-d]pyrimidin-4-one

HRID 1689927Notes

Reaction equation

HRID 1689927 reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=O.[NH3:21]>CO>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([C:11]2[NH:21][C:3](=[O:2])[C:5]3[S:6][CH:7]=[CH:8][C:9]=3[N:10]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 873872HCID 873872, compound

Product 1

HCID 1357964662-(3-methoxy-phenyl)-3H-thieno[3,2-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(3-Methoxy-benzoylamino)-thiophene-2-carboxylic acid methyl ester, 24, (12.78 g) was added to methanol (200 mL) previously saturated with ammonia. The mixture was placed in a bomb reactor, and heated to 100° for 2 days. The solvent was then removed in vacuo and the resulting residue was suspended in isopropanol (250 mL); 2M sodium hydroxide solution was then added (83 mL), and the mixture was heated to reflux for 5 hours. The reaction mixture was then cooled and acidified to pH 1. 2-(3-methoxy-phenyl)-3H-thieno[3,2-d]pyrimidin-4-one, 25, (12.16 g) was collected as a white solid.

Workup

  1. customThe mixture was placed in a bomb reactor
  2. temperatureheated to 100° for 2 days
  3. customThe solvent was then removed in vacuo
  4. addition2M sodium hydroxide solution was then added (83 mL)
  5. temperaturethe mixture was heated
  6. temperatureto reflux for 5 hours
  7. temperatureThe reaction mixture was then cooled
  8. custom2-(3-methoxy-phenyl)-3H-thieno[3,2-d]pyrimidin-4-one, 25, (12.16 g) was collected as a white solid

Sources & evidence

ORD record
ord-a269d4be98f9488e95be337ea57c2cb8
Source dataset
uspto-grants-2012_04
Patent number
US08153639B2

Reaction notes

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