Water → HCID 21931109, compound

HRID 1243967Notes

Reaction equation

HRID 1243967 reaction equation
OC[CH2:3][C:4]1([O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[O:31][N:30]=[C:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[F:38])[N:28]=4)=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:5]1=[O:12].I([O-])(=O)(=O)=O.[Na+].O.C(#N)C.[C:49]([O:52]CC)(=[O:51])[CH3:50]>O.[Ru](Cl)(Cl)Cl>[C:49]([CH2:50][CH2:3][C:4]1([O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[O:31][N:30]=[C:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[F:38])[N:28]=4)=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)[C:5](=[O:12])[NH:6][C:7](=[O:11])[NH:8][C:9]1=[O:10])([OH:52])=[O:51]

Participants

7

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 21931016HCID 21931016, compoundHCID 23667635Sodium periodate

Product 1

HCID 21931109HCID 21931109, compound

Reagents, catalysts & solvents 1

HCID 6093376Ruthenium trichloride hydrateCatalyst

Procedure

A mixture of 5-(2-hydroxy-ethyl)-5-{4-[4-(3-(2-fluorophenyl)-[1,2,4]oxadiazol-5-yl)-phenoxy]-phenoxy}-pyrimidine-2,4,6-trione (518 mg, 1.0 mmol), sodium periodate (875 mg, 4.1 mmol), ruthenium trichloride hydrate (7 mg, 0.025 mmol), water (3 mL), acetonitrile (2 mL), and ethyl acetate (2 mL) was stirred vigorously for 4 hours. The mixture was filtered through diatomaceous earth which was then rinsed with ethyl acetate. The filtrate was washed with 10% sodium dithionite solution and brine and then dried over sodium sulfate. Filtration and concentration yielded 418 mg of the title compound as a white solid. LC-MS (m/z, APCI): 533 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth which
  2. washwas then rinsed with ethyl acetate
  3. washThe filtrate was washed with 10% sodium dithionite solution and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-98ac88e8c92448b68d945e52facb11e8
Source dataset
uspto-grants-2006_10
Patent number
US07119201B2

Reaction notes

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