Sulfuric Acid → HCID 135730618, compound

HRID 354196Notes

Reaction equation

HRID 354196 reaction equation
[Br:1][C:2]1[N:3]([CH3:23])[N:4]=[C:5]2[C:10](=[O:11])[NH:9][C:8]([C:12]3[C:13]([O:20][CH2:21][CH3:22])=[N:14][CH:15]=[C:16]([C:18]#[CH:19])[CH:17]=3)=[N:7][C:6]=12.[OH:24]S(O)(=O)=O>CC(C)=O>[C:18]([C:16]1[CH:17]=[C:12]([C:8]2[NH:9][C:10](=[O:11])[C:5]3[C:6](=[C:2]([Br:1])[N:3]([CH3:23])[N:4]=3)[N:7]=2)[C:13]([O:20][CH2:21][CH3:22])=[N:14][CH:15]=1)(=[O:24])[CH3:19]

Participants

4

Reactant 2

HCID 1118Sulfuric Acid2×HCID 135730635HCID 135730635, compound

Product 1

HCID 135730618HCID 135730618, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-bromo-5-(2-ethoxy-5-ethynyl-3-pyridinyl)-2-methyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (Example 57) (750 mg, 2 mmol), 1N H2SO4 (2 mL) and HgSO4 (50 mg, 0.17 mmol) in acetone (25 mL) was stirred at reflux for 10 h then at room temperature for 14 h. Further H2SO4 (5 mL of 1 N) was added and refluxing was continued for a further 4 h. The mixture was cooled and the solvent evaporated and the residue partitioned between dichloromethane and water. After basifying with solid sodium bicarbonate a white precipitate formed which was filtered off before separating the phases. The organic layer was dried (MgSO4), concentrated and combined with the solid previously filtered to give the title compound as a poorly soluble solid.

Workup

  1. temperatureat reflux for 10 h
  2. temperaturerefluxing
  3. waitwas continued for a further 4 h
  4. temperatureThe mixture was cooled
  5. customthe solvent evaporated
  6. customthe residue partitioned between dichloromethane and water
  7. customformed which
  8. filtrationwas filtered off
  9. custombefore separating the phases
  10. dry with materialThe organic layer was dried (MgSO4)
  11. concentrationconcentrated
  12. filtrationpreviously filtered

Sources & evidence

ORD record
ord-e181ecef7564468a8341359cec237355
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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