Water → HCID 4985365, compound

HRID 856670Notes

Reaction equation

HRID 856670 reaction equation
[SH:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)([O-:17])=[O:16].O>C1COCC1.CN(C=O)C>[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22][S:1][C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 178418793HCID 178418793, compound

Product 1

HCID 4985365HCID 4985365, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

2-mercaptopyrimidine (5.0 g) was dissolved in THF/DMF (150 ml), and to the solution was added triethylamine (7.4 ml) and then 4-nitrobenzyl bromide (8.7 g). The reaction solution was stirred for 1 hour at room temperature, added to water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was washed with hexane/ethyl acetate (=8/1), to give 2-[(4-nitrobenzyl)sulfanyl]pyrimidine (8.0 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. washthe obtained residue was washed with hexane/ethyl acetate (=8/1)

Sources & evidence

ORD record
ord-0f64dc7c4dcb496e8a5cd68636a6f9e6
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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