Sodium periodate → (9-{4-[3-(4-formyl-3-(trifluoromethyl)phenyl)ureido]phenyl}-9H-purin-6-yl)-methylcarbamic acid tert-butyl ester

HRID 1912865Notes

Reaction equation

HRID 1912865 reaction equation
[C:1]([O:5][C:6](=[O:40])[N:7]([CH3:39])[C:8]1[N:16]=[CH:15][N:14]=[C:13]2[C:9]=1[N:10]=[CH:11][N:12]2[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([CH:33]=C)=[C:29]([C:35]([F:38])([F:37])[F:36])[CH:28]=2)=[O:25])=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:42].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[C:1]([O:5][C:6](=[O:40])[N:7]([C:8]1[N:16]=[CH:15][N:14]=[C:13]2[C:9]=1[N:10]=[CH:11][N:12]2[C:17]1[CH:18]=[CH:19][C:20]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[O:42])=[C:29]([C:35]([F:38])([F:36])[F:37])[CH:28]=2)=[O:25])=[CH:21][CH:22]=1)[CH3:39])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 59725915methyl-(9-{4-[3-(3-trifluoromethyl-4-vinylphenyl)ureido]phenyl}-9H-purin-6-yl)-carbamic acid tert-butyl ester

Product 1

HCID 59725906(9-{4-[3-(4-formyl-3-(trifluoromethyl)phenyl)ureido]phenyl}-9H-purin-6-yl)-methylcarbamic acid tert-butyl esterYield 75%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixed solution of 10 mL of tetrahydrofuran and 5 mL of water, 324 mg (0.59 mmol) of methyl-(9-{4-[3-(3-trifluoromethyl-4-vinylphenyl)ureido]phenyl}-9H-purin-6-yl)-carbamic acid tert-butyl ester was dissolved, and 200 μL of a 0.1 M osmium tetraoxide aqueous solution and 510 mg (2.38 mmol) of sodium periodate were added thereto, and the mixture solution was stirred at room temperature for 14 hours. The reaction solution was partitioned between water and ethyl acetate, and the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The product was purified by a silica gel column (hexane:ethyl acetate=1:2) to obtain 243 mg (75%) of a target product as a white crystal.

Workup

  1. customThe reaction solution was partitioned between water and ethyl acetate
  2. washthe organic layer was washed with a saturated sodium chloride solution
  3. concentrationconcentrated under reduced pressure
  4. customThe product was purified by a silica gel column (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-7a810b8f019f4a02a087f0ca9706a57d
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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