N-Methylmorpholine N-oxide monohydrate → HCID 86723433, compound

HRID 2201190Notes

Reaction equation

HRID 2201190 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[N:10]([N:15]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:22]2[C:17]([N:18]([CH3:33])[C:19](=[O:32])[N:20]([CH3:31])[C:21]2=[O:30])=[CH:16]1)[CH2:11][CH2:12][CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C[N+]1([O-])CC[O:40]CC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([O:8][C:9]([N:10]([N:15]1[C:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:22]2[C:17]([N:18]([CH3:33])[C:19](=[O:32])[N:20]([CH3:31])[C:21]2=[O:30])=[CH:16]1)[CH2:11][CH2:12][C:13]([OH:40])=[O:14])=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 86723432HCID 86723432, compound

Product 1

HCID 86723433HCID 86723433, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

Tetrapropylammonium perruthenate (0.152 g, 0.432 mmol) was added to a solution of (1,3-Dimethyl-2,4-dioxo-5-phenyl-1,2,3,4-tetrahydro-pyrrolo[3,4-d]pyrimidin-6-yl)-(3-hydroxy-propyl)-carbamic acid benzyl ester (step 2) (2 g, 4.32 mmol) and N-methylmorpholine oxide monohydrate (commercial) (2.92 g, 21.62 mmol) in Acetonitrile (40 ml). The mixture was stirred at room temp. for 30 mins. The reaction mixture was quenched with isopropanol (50 mL) and stirred for 20 mins. The mixture was then evaporated under reduced pressure. Purification of the residue by chromatography on silica, eluting with EtOAc followed by 1% acetic acid/EtOAc afforded the title compound as a white solid.

Workup

  1. customThe reaction mixture was quenched with isopropanol (50 mL)
  2. stirringstirred for 20 mins
  3. customThe mixture was then evaporated under reduced pressure
  4. customPurification of the residue by chromatography on silica
  5. washeluting with EtOAc

Sources & evidence

ORD record
ord-201942bb0b2f49af8f5902dc4bead521
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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