HCID 11363485, compound → HCID 23154929, compound

HRID 1912845Notes

Reaction equation

HRID 1912845 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([CH:32]=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.I([O-])(=O)(=O)=[O:35].[Na+]>O1CCCC1.O.[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:5]([CH:32]=[O:35])[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

6

Reactant 2

HCID 11363485HCID 11363485, compoundHCID 23667635Sodium periodate

Product 1

HCID 23154929HCID 23154929, compoundYield 94.6%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixed solution of 4 mL of tetrahydrofuran and 1 mL of water, 20 mg (0.04 mmol) of 1-[4-(6-amino-8-vinyl-purin-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 40 mg (0.19 mmol) of sodium periodate 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 18 mg (90%) 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-265794ffac3046bfb6602c9aaa3d2a7d
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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