Sodium periodate → HCID 68524098, compound

HRID 1863924Notes

Reaction equation

HRID 1863924 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[F:7][C:8]([F:27])([F:26])[C:9]1[N:10]=[CH:11][C:12]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C:13]=2[N:14]=1>C(OCC)(=O)C.[Ru](=O)=O>[O:2]=[C:15]1[C:13]2[N:14]=[C:9]([C:8]([F:7])([F:26])[F:27])[N:10]=[CH:11][C:12]=2[CH2:18][CH2:17][N:16]1[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 68523669HCID 68523669, compound

Product 1

HCID 68524098HCID 68524098, compound

Reagents, catalysts & solvents 2

HCID 82848Ruthenium dioxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 51 mg (0.328 mmol) of ruthenium dioxide and 25.9 mL (11.9 mmol) of 10% sodium periodate aqueous solution was added a solution of 766 mg (2.53 mmol) of tert-butyl 2-(trifluoromethyl)-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate in 20 mL of ethyl acetate. The mixture was stirred vigorously for 4 h and then partitioned between ethyl acetate and water. The aqueous phase was extracted with 2 additional portions of ethyl acetate. The combined organic fractions were concentrated. Flash chromatography of the residue on silica gel (9:1 hexanes/ethyl acetate) afforded material that was collected on a filter and washed with diethyl ether to give the title compound as a white solid. LC-MS 318 (M+1).

Workup

  1. custompartitioned between ethyl acetate and water
  2. extractionThe aqueous phase was extracted with 2 additional portions of ethyl acetate
  3. concentrationThe combined organic fractions were concentrated
  4. customFlash chromatography of the residue on silica gel (9:1 hexanes/ethyl acetate) afforded material that
  5. customwas collected on
  6. filtrationa filter
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-e55eaba06ce64d5a8bdd1cfc428a4992
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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