Sodium Thiosulfate → HCID 178504208, compound

HRID 1506257Notes

Reaction equation

HRID 1506257 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]2[C:14]3[C:15]4[CH:21]=[CH:20][N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:16]=4[N:17]=[CH:18][C:13]=3[C:12](=[O:30])[NH:11][C:10]2=[O:31])[CH2:5][CH2:4]1.I(C1C=CC=CC=1C(O)=O)(=O)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.CS(C)=O>[O:31]=[C:10]1[N:9]([C@H:6]2[CH2:7][CH2:8][C@H:3]([CH:2]=[O:1])[CH2:4][CH2:5]2)[C:14]2[C:15]3[CH:21]=[CH:20][N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:28])([CH3:27])[CH3:29])[C:16]=3[N:17]=[CH:18][C:13]=2[C:12](=[O:30])[NH:11]1

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 1087942-Iodoxybenzoic acidHCID 516892Sodium BicarbonateHCID 178504209HCID 178504209, compound

Product 1

HCID 178504208HCID 178504208, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

1-[trans-4-(Hydroxymethyl)cyclohexyl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[3′,2′:5,6]pyrido[4,3-d]pyrimidine-2,4(3H,7H)-dione (107 mg, 0.240 mmol) in a mixture of toluene (1 mL) and dimethyl sulfoxide (0.25 mL) was mixed with 2-iodoxybenzoic acid (80.9 mg, 0.288 mmol) and stirred at 50° C. for 2 hours. After addition of saturated aqueous sodium thiosulfate and saturated aqueous sodium hydrogen carbonate, the reaction mixture was stirred at room temperature for 30 minutes, and extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1→7/3 (v/v)) to give the title compound as a colorless solid (70.1 mg, yield 66%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1→7/3 (v/v))

Sources & evidence

ORD record
ord-682dfb62b9af4e0a9c933c7f63978539
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

Loading…