O-Toluidine → HCID 18350688, compound

HRID 430521Notes

Reaction equation

HRID 430521 reaction equation
[CH3:1][C:2]1O[C:4](=[O:11])[C:5]2[C:6](=[CH:8][S:9][CH:10]=2)[N:7]=1.[NH2:12][C:13]1[C:14]([CH3:19])=[CH:15][CH:16]=[CH:17][CH:18]=1>C(O)(=O)C>[CH3:1][C:2]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[C:4](=[O:11])[C:5]2[C:6](=[CH:8][S:9][CH:10]=2)[N:7]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 15425486HCID 15425486, compound

Product 1

HCID 18350688HCID 18350688, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a slurry of 2-methyl-thieno[3,4-d][1,3]oxazin-4-one (1.0 g, 5.99 mmol) and acetic acid (15 mL) was added o-toluidine (1.2 mL, 10.78 mmol). The mixture was refluxed 3 hours, cooled, and concentrated. The residue was partitioned between ethyl acetate and water and the aqueous phase was made basic by careful addition of saturated aqueous sodium bicarbonate. The phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over sodium sulfate and concentrated to a black oil. The oil was flash chromatographed on silica gel (30×100 mm) eluting with 20% ethyl acetate/hexane. Product fractions were combined to afford 0.303 g of 2-methyl-3-o-tolyl-3H-thieno[3,4-d]pyrimidin-4-one as a tan oil which solidified on standing.

Workup

  1. temperatureThe mixture was refluxed 3 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe residue was partitioned between ethyl acetate and water
  5. additionthe aqueous phase was made basic by careful addition of saturated aqueous sodium bicarbonate
  6. customThe phases were separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washThe combined organic layer was washed with water and brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated to a black oil
  11. customchromatographed on silica gel (30×100 mm)
  12. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-04211984997d4ccdb1e2e4f05e02c113
Source dataset
uspto-grants-2001_11
Patent number
US06323208B1

Reaction notes

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