CID 86596527 → (3-(2-(4-bromophenyl)-1-(4-chlorophenyl)-6-oxo-1H-purin-9(6H)-yl)phenylsulfonyl)methyl acetate

HRID 1024622Notes

Reaction equation

HRID 1024622 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[C:10](=[O:29])[C:11]3[N:12]=[CH:13][N:14]([C:17]4[CH:18]=[C:19]([S:23][CH2:24][O:25][C:26](=[O:28])[CH3:27])[CH:20]=[CH:21][CH:22]=4)[C:15]=3[N:16]=2)=[CH:4][CH:3]=1.C(O)(=O)C.[OH2:41].[OH2:42].O.O.O.O.C1(=O)OOOOC(=O)C2=CC=CC=C12.[Mg]>CO.ClCCl>[C:26]([O:25][CH2:24][S:23]([C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([N:14]2[CH:13]=[N:12][C:11]3[C:10](=[O:29])[N:9]([C:30]4[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=4)[C:8]([C:5]4[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=4)=[N:16][C:15]2=3)[CH:18]=1)(=[O:42])=[O:41])(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 86596527CID 86596527HCID 131731396acetic acid (3-(2-(4-bromophenyl)-1-(4-chlorophenyl)-6-oxo-1H-purin-9(6H)-yl)phenylthio)methyl acetate

Product 1

HCID 57899397(3-(2-(4-bromophenyl)-1-(4-chlorophenyl)-6-oxo-1H-purin-9(6H)-yl)phenylsulfonyl)methyl acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of acetic acid (3-(2-(4-bromophenyl)-1-(4-chlorophenyl)-6-oxo-1H-purin-9(6H)-yl)phenylthio)methyl acetate (3, 2.1 g, 3.6 mmol) in methanol (12 mL), dichloromethane (36 mL), magnesium monoperoxy phthalate hexahydrate (1.9 g, 3.97 mmol) is added at 0° C. The resulting solution is stirred at rt for 12 h. The reaction is quenched with the addition of saturated solution of sodium bicarbonate, and extracted with dichloromethane. The organic layer is dried over Na2SO4, concentrated. The crude product is purified by column chromatography to afford (3-(2-(4-bromophenyl)-1-(4-chlorophenyl)-6-oxo-1H-purin-9(6H)-yl)phenylsulfonyl)methyl acetate (4).

Workup

  1. customThe reaction is quenched with the addition of saturated solution of sodium bicarbonate
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-95a9db6860084cd4b9f8baa759799f62
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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