Tetrahydrofuran → 4,6-Dimethyl-2-[(4-nitrobenzyl)sulfanyl]pyrimidine

HRID 856686Notes

Reaction equation

HRID 856686 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([SH:9])[N:3]=1.C1COCC1.C(N(CC)CC)C.[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([O-:24])=[O:23]>O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH2:29][C:28]2[CH:31]=[CH:32][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)[N:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 1784266324,6-dimethylpyrimidine-2-thiol

Product 1

HCID 5725194,6-Dimethyl-2-[(4-nitrobenzyl)sulfanyl]pyrimidineYield 56.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4,6-dimethylpyrimidine-2-thiol (9.1 g) was added THF (70 ml), and to this solution was added triethylamine (21.5 ml) and then, 4-nitrobenzyl bromide (10 g), and the mixture was stirred for 5 hours at 50° C. After cooling to room temperature, the mixture was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the obtained residue was washed with hexane/ethyl acetate, to give 4,6-dimethyl-2-[(4-nitrobenzyl)sulfanyl]pyrimidine (7.2 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 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

Sources & evidence

ORD record
ord-07ccde13f34844d6b2f5bfe783c9854c
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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