Chlorosuccinimide → 6-Chloro-7-[4-(4-chlorobenzoyl)benzyl]-3,5-dimethyl-2-methylthio-7H-pyrrolo [2,3-d]pyrimidin-4(3H)-one

HRID 1291304Notes

Reaction equation

HRID 1291304 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([C:8]2[CH:28]=[CH:27][C:11]([CH2:12][N:13]3[C:17]4[N:18]=[C:19]([S:24][CH3:25])[N:20]([CH3:23])[C:21](=[O:22])[C:16]=4[C:15]([CH3:26])=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[Cl:31]N1C(=O)CCC1=O>ClCCl>[Cl:31][C:14]1[N:13]([CH2:12][C:11]2[CH:27]=[CH:28][C:8]([C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:30][CH:29]=3)=[CH:9][CH:10]=2)[C:17]2[N:18]=[C:19]([S:24][CH3:25])[N:20]([CH3:23])[C:21](=[O:22])[C:16]=2[C:15]=1[CH3:26]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 18919182HCID 18919182, compound

Product 1

HCID 699619986-Chloro-7-[4-(4-chlorobenzoyl)benzyl]-3,5-dimethyl-2-methylthio-7H-pyrrolo [2,3-d]pyrimidin-4(3H)-oneYield 57.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In anhydrous dichloromethane (3 ml) was dissolved 7-[4-(4-chlorobenzoyl)benzyl]-3,5-dimethyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (88 mg) and, under ice-cooling and stirring, N-chlorosuccinimide (28 mg) was added. After 2 hours of stirring, the solvent was distilled off under reduced pressure and the residue was purified by flash column chromatography (silica gel; chloroform) to provide the title compound (55 mg).

Workup

  1. temperatureunder ice-cooling
  2. stirringAfter 2 hours of stirring
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe residue was purified by flash column chromatography (silica gel; chloroform)

Sources & evidence

ORD record
ord-7d987e96a8ae49c4bf88cf896959c10b
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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