HCID 16656820, compound → HCID 58022222, compound

HRID 578813Notes

Reaction equation

HRID 578813 reaction equation
[OH:1][CH2:2][C:3]1[S:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]1[CH:18]=[C:17]([S:19]([N:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25][CH2:24][CH2:23]3)(=[O:21])=[O:20])[CH:16]=[CH:15][C:14]=1[Cl:32])[C:8](=[O:33])[NH:7]2>CN(C)C=O.C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[S:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]1[CH:18]=[C:17]([S:19]([N:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25][CH2:24][CH2:23]3)(=[O:20])=[O:21])[CH:16]=[CH:15][C:14]=1[Cl:32])[C:8](=[O:33])[NH:7]2)=[O:1]

Participants

5

Reactant 1

HCID 16656820HCID 16656820, compound

Product 1

HCID 58022222HCID 58022222, compoundYield 41.7%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-hydroxymethyl-3-[2-chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]thieno[3,4-d]-pyrimidine-2,4(1H,3H)-dione (77 mg) in N,N-dimethylformamide (2.1 mL) was added manganese (IV) dioxide (0.77 g), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, and the insoluble material was removed by filtration. The filtrate was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1) to give the title compound (32 mg).

Workup

  1. customthe insoluble material was removed by filtration
  2. washThe filtrate was washed with water and brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-515e458edba6438abaef0ee5c9370da4
Source dataset
uspto-grants-2015_05
Patent number
US09040693B2

Reaction notes

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