Hydrogen Peroxide → HCID 23155017, compound

HRID 1912843Notes

Reaction equation

HRID 1912843 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=C(C=C)[N:6]2[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=2)=[O:19])=[CH:13][CH:12]=1.[OH:34]O.[O:36]1[CH2:40][CH2:39][CH2:38]C1>[Os](=O)(=O)(=O)=O>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:38]([CH:39]([OH:34])[CH2:40][OH:36])[N:6]2[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=2)=[O:19])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 11363485HCID 11363485, compound

Product 1

HCID 23155017HCID 23155017, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

In 1 mL of tetrahydrofuran, 20 mg (0.04 mmol) of 1-[4-(6-amino-8-vinylpurin-9-yl)phenyl]-3-(4-chloro-3-(trifluoromethyl)phenyl)urea was dissolved, and 20 μL of a 0.1 M osmium tetraoxide aqueous solution and 143 μL of a 3% hydrogen peroxide aqueous solution were added thereto, and the mixture solution was stirred at room temperature for 14 hours. The reaction solution was concentrated under reduced pressure and purified by a silica gel column (dichloromethane:methanol=9:1) to obtain 16.4 mg (77%) of a target product as a white crystal.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. custompurified by a silica gel column (dichloromethane:methanol=9:1)

Sources & evidence

ORD record
ord-60c86555dfec4dfbb46db69f6cb46eaf
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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