1-(Bromomethyl)-4-chlorobenzene → HCID 89690253, compound

HRID 2202844Notes

Reaction equation

HRID 2202844 reaction equation
[N:1]1[C:6]([OH:7])=[CH:5][C:4]([OH:8])=[N:3][CH:2]=1.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1>C1COCC1.C(=O)([O-])[O-].[Ag+2]>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][O:8][C:4]2[N:3]=[CH:2][NH:1][C:6](=[O:7])[CH:5]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 178516651HCID 178516651, compound

Product 1

HCID 89690253HCID 89690253, compoundYield 9.5%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of pyrimidine-4,6-diol (2.5 g) in THF (25 ml) was added silver carbonate (15.3 g) at room temperature followed by dropwise addition of 4-chlorobenzyl bromide (4.58 g), and the resultant mixture was heated at reflux for 2 h. The reaction mixture was then cooled to room temperature, filtered through Celite, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (500 mg) as a white solid.

Workup

  1. temperatureat reflux for 2 h
  2. filtrationfiltered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-c04412cd083248258b5c08f35f509fe7
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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