Water → HCID 52933693, compound

HRID 2401325Notes

Reaction equation

HRID 2401325 reaction equation
[CH:1]1([C:6]2[NH:14][C:13]3[C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH3:18])[C:10]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=4)=[N:9][C:8]=3[N:7]=2)[CH2:5][CH:4]=[CH:3][CH2:2]1.C[N+]1([O-])CC[O:32]CC1.C(O)(C)(C)C.[OH2:41]>CC(C)=O.[Os](=O)(=O)(=O)=O>[OH:41][CH:3]1[CH:4]([OH:32])[CH2:5][CH:1]([C:6]2[NH:14][C:13]3[C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH3:18])[C:10]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=4)=[N:9][C:8]=3[N:7]=2)[CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 67202935HCID 67202935, compound

Product 1

HCID 52933693HCID 52933693, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of 8-cyclopent-3-enyl-2-(3-methoxy-phenoxy)-1-propyl-1,7-dihydro-purin-6-one (0.075 g, 0.20 mmol) and N-methyl morpholine N-oxide (0.036 g, 0.30 mmol) in a mixture of acetone, t-butanol, and water in the ratio 60:1:1, catalytic amount of osmium tetroxide (2 mg) was added. Reaction mixture was allowed to stir for 2 hours at room temperature. The reaction mixture was quenched with saturated sodium sulphite solution and was diluted with ethyl acetate and water. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulphate and concentrated under vacuum. The crude product was purified by preparative TLC using 3% methanol in DCM to give the product (0.014 g, 13%) as light green solid.

Workup

  1. additionwas added
  2. customReaction mixture
  3. customThe reaction mixture was quenched with saturated sodium sulphite solution
  4. additionwas diluted with ethyl acetate and water
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-f62a9e5fd19244d2b2ed9e54ccbe4671
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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