Water → 7-(1-(4-Chlorothiazol-2-yl)-3,4-dihydroxybutyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2201258Notes

Reaction equation

HRID 2201258 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH:7]([C:11]2[NH:12][C:13]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=3)=[C:14]3[C:19](=[O:20])[N:18]([CH3:21])[C:17](=[O:22])[N:16]([CH3:23])[C:15]=23)[CH2:8][CH:9]=[CH2:10])[S:5][CH:6]=1.C[N+]1([O-])CC[O:35]CC1.[OH2:39]>C(#N)C.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[N:3]=[C:4]([CH:7]([C:11]2[NH:12][C:13]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=3)=[C:14]3[C:19](=[O:20])[N:18]([CH3:21])[C:17](=[O:22])[N:16]([CH3:23])[C:15]=23)[CH2:8][CH:9]([OH:35])[CH2:10][OH:39])[S:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 867234987-(1-(4-Chlorothiazol-2-yl)but-3-en-1-yl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 867234997-(1-(4-Chlorothiazol-2-yl)-3,4-dihydroxybutyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6342AcetonitrileSolvent

Procedure

Osmium tetroxide (2.5% w.t., 2.032 mL, 0.162 mmol) was added to a solution of 7-(1-(4-chlorothiazol-2-yl)but-3-en-1-yl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (720 mg, 1.618 mmol) and N-methyl morpholine oxide (284 mg, 2.427 mmol) in acetonitrile (20 mL,) and water (2 mL). The mixture was stirred at room temperature for 105 mins. The reaction was quenched with saturated aqueous sodium metabisulfite solution and extracted with chloroform (3×). The combined organic extracts were passed through a hydrophobic frit and evaporated under vacuum to afford the title compound as a mixture of diastereomers.

Workup

  1. customThe reaction was quenched with saturated aqueous sodium metabisulfite solution
  2. extractionextracted with chloroform (3×)
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-b4dd0d736aed478fa398539a2d7930ef
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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