Dimethylformamide → HCID 18918802, compound

HRID 1291248Notes

Reaction equation

HRID 1291248 reaction equation
[SH:1][C:2]1[N:3]([CH3:13])[C:4](=[O:12])[C:5]2[C:10]([CH3:11])=[N:9][O:8][C:6]=2[N:7]=1.[OH-].[Na+].CN(C=O)C.[Cl:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1>C(O)C>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32][S:1][C:2]3[N:3]([CH3:13])[C:4](=[O:12])[C:5]4[C:10]([CH3:11])=[N:9][O:8][C:6]=4[N:7]=3)=[CH:30][CH:29]=2)=[O:27])=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 178434714HCID 178434714, compound

Product 1

HCID 18918802HCID 18918802, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-mercapto-3,5-dimethylisoxazolo-[5,4-d]pyrimidin-4(5H)-one (800 mg) and sodium hydroxide (165 mg) in 50% ethanol (10 ml)-DMF (10 ml) was added 4-(4-chlorobenzoyl)benzyl bromide (1.25 g) and the mixture was stirred at room temperature for 1 hour. This reaction mixture was concentrated and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to provide the title compound as colorless solid (470 mg). 1H-NMR (CDCl3) 8: 2.57(3H,s), 3.55(3H,s), 4.59(2H,s), 7.46(2H,d,J=8.6Hz), 7.58(2H,d,J=8.4Hz), 7.74(2H,d,J=8.4Hz), 7.76(2H,d,J=8.6Hz).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-94cf29a00d914caa87aa72aa4b7f2abf
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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