Sodium Hydroxide → 2-[4-(4-Fluorobenzoyl)benzyl]thio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

HRID 1291312Notes

Reaction equation

HRID 1291312 reaction equation
[SH:1][C:2]1[NH:3][C:4](=[O:11])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[OH-].[Na+].[F:14][C:15]1[CH:30]=[CH:29][C:18]([C:19]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=2)=[O:20])=[CH:17][CH:16]=1>CO.COCCOC>[F:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25][S:1][C:2]3[NH:3][C:4](=[O:11])[C:5]4[CH:10]=[CH:9][NH:8][C:6]=4[N:7]=3)=[CH:23][CH:22]=2)=[O:20])=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 47290134-(4-Fluorobenzoyl)benzyl bromideHCID 178518762HCID 178518762, compound

Product 1

HCID 1356675972-[4-(4-Fluorobenzoyl)benzyl]thio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-oneYield 42.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

In methanol (65.7 ml) was suspended 2-mercapto-7H-pyrrolo [2,3-d]pyrimidin-4(3H)-one (2.51 g) followed by addition of 1N-sodium hydroxide (15.75 ml) for dissolution. Then, a solution of 4-(4-fluorobenzoyl)benzyl bromide (5.06 g) in DME (15 ml) was added dropwise with ice-cooling. Then, the mixture was stirred at room temperature overnight. The solvent was then distilled off under reduced pressure and the residue was purified by flash column chromatography (silica gel; ethyl acetate: hexane=1:4-1:1-ethyl acetate) to provide the title compound (2.43 g).

Workup

  1. temperaturecooling
  2. distillationThe solvent was then distilled off under reduced pressure
  3. customthe residue was purified by flash column chromatography (silica gel; ethyl acetate: hexane=1:4-1:1-ethyl acetate)

Sources & evidence

ORD record
ord-682556ddd3c6480dbe2053d40307987a
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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