Water → HCID 22636410, compound

HRID 2415691Notes

Reaction equation

HRID 2415691 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16](=[O:17])[N:11]3[CH2:12][CH:13]=[CH:14][CH2:15][N:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[N:19]=2)=[CH:4][CH:3]=1.[OH2:33].C([O-])([O-])=[O:35].[K+].[K+].C([O-])(O)=O.[Na+]>CC(O)(C)C.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16](=[O:17])[N:11]3[CH2:12][CH:13]([OH:35])[CH:14]([OH:33])[CH2:15][N:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[N:19]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 10296114HCID 10296114, compound

Product 1

HCID 22636410HCID 22636410, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-3-[2-(1-phenylethylamino)pyrimidin-4-yl]-5,8-dihydro-pyrazolo[1,2-a]pyridazin-1-one, 13, (0.8 g, 1.88 mmol) in t-BuOH:H2O (24 mL of 1:1 mixture) is added K3Fe(CN)6 (1.9 g, 5.64 mmol), K2CO3 (0.8 g, 5.6 mmol) and NaHCO3 (0.5 g, 5.6 mmol), followed by osmium tetroxide (0.1 g, 0.3 mmol). The resulting mixture is stirred at room temperature for 12 hours. The reaction is quenched by the addition of aqueous saturated KHSO4 solution (10 mL). The aqueous phase is extracted with EtOAc (3×) and the combined organic phases are dried, filtered and concentrated in vacuo. The resulting crude product is purified over silica (100% EtOAc) to afford 0.4 g (48% yield) of the desired product.

Workup

  1. customThe reaction is quenched by the addition of aqueous saturated KHSO4 solution (10 mL)
  2. extractionThe aqueous phase is extracted with EtOAc (3×)
  3. customthe combined organic phases are dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude product is purified over silica (100% EtOAc)

Sources & evidence

ORD record
ord-8001e785280b427895bb30d4b614906e
Source dataset
uspto-grants-2004_11
Patent number
US06821971B2

Reaction notes

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