Acetic Anhydride → HCID 69709047, compound

HRID 1737248Notes

Reaction equation

HRID 1737248 reaction equation
[CH3:1][C:2]1[N:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:4](=[O:11])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C(OC(=O)C)(=O)C.[F:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH:29]=O>[Cl-].[Zn+2].[Cl-]>[CH3:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:3]1[C:4](=[O:11])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:2]1[CH:1]=[CH:29][C:28]1[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=1[F:26]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 67970o-FluorobenzaldehydeHCID 9016182-Methyl-3-(2-methylphenyl)thieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 69709047HCID 69709047, compoundYield 136.9%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Anhydrous zinc chloride (7.0 g, 51.4 mmol) was fused with a nitrogen purge in a round bottom flask with an open flame. The reaction vessel was allowed to return to ambient temperature, then dioxane (100 mL) was added. To this mixture was added 2-methyl-3-(2-methylphenyl)-3H-thieno[3,2-d]pyrimidin-4-one (7.0 g, 27.34 mmol, preparation 2), acetic anhydride (7.7 mL, 82.0 mmol), and 2-fluorobenzaldehyde (8.6 mL, 10.2 mmol). The reaction was refluxed 14 hours, cooled to ambient temperature, and partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combined organic layer was filtered to obtain a small amount of product which had precipitated. The filtrate was washed with water and brine, dried over magnesium sulfate and concentrated to leave a mustard colored solid. This material was added to the product which had previously been collected and the combined material was flash chromatographed on silica gel (60×185 mm) eluting with 25-40% ethyl acetate/hexane to afford 5.06 g (51%) of 3-(2-methyl-phenyl)-2-[2-(2-fluoro-phenyl)-vinyl]-3H-thieno[3,2-d]pyrimidin-4-one as a light yellow solid.

Workup

  1. custompurge in a round bottom flask with an open flame
  2. customto return to ambient temperature
  3. additiondioxane (100 mL) was added
  4. temperatureThe reaction was refluxed 14 hours
  5. custompartitioned between ethyl acetate and water
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. filtrationthe combined organic layer was filtered
  8. customto obtain a small amount of product which
  9. customhad precipitated
  10. washThe filtrate was washed with water and brine
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated
  13. customto leave a mustard
  14. additionThis material was added to the product which
  15. customhad previously been collected
  16. customchromatographed on silica gel (60×185 mm)
  17. washeluting with 25-40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a5cc849e4770403f965725903c928d64
Source dataset
uspto-grants-1999_10
Patent number
US05962457

Reaction notes

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