Acetic Anhydride → HCID 69710341, compound

HRID 1737249Notes

Reaction equation

HRID 1737249 reaction equation
O1CCOCC1.[CH3:7][C:8]1[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[C:10](=[O:17])[C:11]2[S:16][CH:15]=[CH:14][C:12]=2[N:13]=1.C(OC(=O)C)(=O)C.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH:38]=O>C(=O)(O)[O-].[Na+]>[CH3:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[N:9]1[C:10](=[O:17])[C:11]2[S:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:8]1[CH:7]=[CH:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 142732-PyridinecarboxaldehydeHCID 312751,4-DioxaneHCID 9016182-Methyl-3-(2-methylphenyl)thieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 69710341HCID 69710341, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of fused zinc chloride (2.13 g, 15.6 mmol) and dioxane (75 mL), 2-methyl-3-(2-methylphenyl)-3H-thieno[3,2-d]pyrimidin-4-one (2.0 g, 7.81 mmol, preparation 2), and acetic anhydride (2.2 mL, 23.4 mmol) was added 2-pyridine carboxaldehyde (2.2 mL, 23.4 mmol). The reaction was refluxed 1.5 hours, cooled to ambient temperature, and diluted with aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate and the organic extracts were washed with water and brine, dried over sodium sulfate and concentrated to leave a dark residue. This material was flash chromatographed on silica gel (45×125 mm). Elution with 20% ethyl acetate/hexane removed an unweighed impurity. Continued elution with 40% ethyl acetate/hexane gave a sticky yellow foam. The foam was triturated with 5% ethyl acetate/hexane to yield 1.9 g (70%) of 3-(2-methyl-phenyl)-2-[2-pyrid-2-yl-vinyl]-3H-thieno[3,2-d]pyrimidin-4-one as a yellow solid.

Workup

  1. temperatureThe reaction was refluxed 1.5 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto leave a dark residue
  7. customchromatographed on silica gel (45×125 mm)
  8. washElution with 20% ethyl acetate/hexane
  9. customremoved an unweighed impurity
  10. washelution with 40% ethyl acetate/hexane
  11. customgave a sticky yellow foam
  12. customThe foam was triturated with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f352294c5a784ab69190a55c068b71e6
Source dataset
uspto-grants-1999_10
Patent number
US05962457

Reaction notes

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