Water → HCID 69448731, compound

HRID 1296725Notes

Reaction equation

HRID 1296725 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[N:10]([C:11]([S:17][CH3:18])=[N:12][CH:13]=[CH:14]3)[N:9]=2)=[CH:4][CH:3]=1.O.[C:20](OC(=O)C)(=[O:22])[CH3:21]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]([C:20](=[O:22])[CH3:21])=[C:15]3[N:10]([C:11]([S:17][CH3:18])=[N:12][CH:13]=[CH:14]3)[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 17956316HCID 17956316, compound

Product 1

HCID 69448731HCID 69448731, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
110 °C

Procedure

To a slurry of 2-(4-fluorophenyl)-7-(methylsulfanyl)pyrazolo[1,5-c]pyrimidine (1.5 g, 5.9 mmol) in acetic anhydride (10 mL) was added 4 drops of sulfuric acid. The reaction mixture was heated to 80° C. for 2 hours, to 110° C. for 2 hours, and to reflux for 2 hours. The solution was allowed to cool to room temperature and stirred for 4 days. The mixture was poured into water (350 mL) and extracted with ethyl acetate (2×75 mL). The organic phase was washed with brine and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 2:98 acetone:dichloromethane to yield 1-[2-(4-fluorophenyl)-7-(methylsulfanyl)pyrazolo[1,5-c]pyrimidin-3-yl]ethanone (1.24 g, 70%). 1H NMR (DMSO): δ 8.12 (d, 1H), 7.98 (d, 1H), 7.65 (dd, 2H), 7.24 (m, 2H), 2.77 (s, 3H), 2.23 (s, 3H). MS m/z302 (M+1).

Workup

  1. temperatureto reflux for 2 hours
  2. temperatureto cool to room temperature
  3. extractionextracted with ethyl acetate (2×75 mL)
  4. washThe organic phase was washed with brine
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 2:98 acetone

Sources & evidence

ORD record
ord-3a8cc762ec3540368ddb0ac2aaa137c7
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

Loading…