Acetic Anhydride → HCID 135871516, compound

HRID 1689929Notes

Reaction equation

HRID 1689929 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:9][C:10](=[O:17])[C:11]3[S:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:18][C:19]([O-])=[O:20].[K+].CC(OC(C)=O)=O>CC#N>[O:17]=[C:10]1[NH:9][C:8]([C:4]2[CH:3]=[C:2]([O:1][C:19](=[O:20])[CH3:18])[CH:7]=[CH:6][CH:5]=2)=[N:13][C:12]2[CH:14]=[CH:15][S:16][C:11]1=2

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517044Potassium AcetateHCID 135863375HCID 135863375, compound

Product 1

HCID 135871516HCID 135871516, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(3-hydroxy-phenyl)-3H-thieno[3,2-d]pyrimidin-4-one, 26, (10.95 g, 44.8 mmol), KOAc (6.6 g, 67.2 mmol) and Ac2O (16.5 mL, 0.175 mol) in MeCN (150 mL) were heated at reflux temperature for 24 h. The cooled reaction mixture was poured onto water (500 mL) and the resulting precipitate was collected by filtration. This was then washed with water and dried to furnish acetic acid 3-(4-oxo-3,4-dihydro-thieno[3,2-d]pyrimidin-2-yl)-phenyl ester, 27, as a grey solid (10.87 g, 85%).

Workup

  1. temperaturewere heated
  2. temperatureat reflux temperature for 24 h
  3. customThe cooled reaction mixture
  4. additionwas poured onto water (500 mL)
  5. filtrationthe resulting precipitate was collected by filtration
  6. washThis was then washed with water
  7. customdried

Sources & evidence

ORD record
ord-c7fcba8ba6104f178fb32fd125399c00
Source dataset
uspto-grants-2012_04
Patent number
US08153639B2

Reaction notes

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