Iodine → HCID 90197167, compound

HRID 576778Notes

Reaction equation

HRID 576778 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[C:8]([C:11]2[N:15]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[N:14]=[CH:13][CH:12]=2)=[C:7]([CH3:24])[N:6]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[C:5]1=[O:35])([CH3:3])[CH3:2].[I:36]I.[N+]([O-])([O-])=O.[NH4+].[Ce].S([O-])(O)=O.[Na+]>C(#N)C.C(OCC)(=O)C>[I:36][C:12]1[CH:13]=[N:14][N:15]([C:16]2[CH:17]=[CH:18][C:19]([C:20]#[N:21])=[CH:22][CH:23]=2)[C:11]=1[C:8]1[C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:35])[N:6]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[C:7]=1[CH3:24]

Participants

7

Reactant 4

HCID 807IodineHCID 23665763Sodium BisulfiteHCID 57418452Ammonium cerium-nitrateHCID 71513632HCID 71513632, compound

Product 1

HCID 90197167HCID 90197167, compoundYield 153.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 4-(5-(3-isopropyl-6-methyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (prepared in Example 42) (0.82 g) in acetonitrile (15 ml) were added iodine (0.26 g) and cerium ammonium nitrate (0.56 g) and the resulting mixture was stirred at 50° C. for one hour. The reaction mixture was cooled to room temperature, and thereto were added ethyl acetate (50 ml) and 5% aqueous sodium hydrogen sulfite solution (25 ml), and the mixture was partitioned. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 4-(4-iodo-5-(3-isopropyl-6-methyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (0.95 g) as white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe mixture was partitioned
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b69be06ad92d4beaa4ef71b75e213fc8
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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