Water → (3-Chlorophenyl)(4,6-dimethoxypyrimidin-2-yl)acetonitrile

HRID 846538Notes

Reaction equation

HRID 846538 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7](S(C)(=O)=O)[N:6]=1.[Cl:17][C:18]1[CH:19]=[C:20]([CH2:24][C:25]#[N:26])[CH:21]=[CH:22][CH:23]=1.O>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[C:20]([CH:24]([C:7]2[N:6]=[C:5]([O:4][CH3:3])[CH:10]=[C:9]([O:11][CH3:12])[N:8]=2)[C:25]#[N:26])[CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 73722m-ChlorophenylacetonitrileHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidine

Product 1

HCID 19882861(3-Chlorophenyl)(4,6-dimethoxypyrimidin-2-yl)acetonitrileYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

Sodium hydride (6.0 g of 80% in oil) was added portionwise to a stirred solution of 4,6-dimethoxy-2-(methylsulphonyl)pyrimidine (21.8 g) and (3-chlorophenyl)acetonitrile (15.1 g) in dry dimethylformamide (150 ml) at 5° C. The mixture was stirred at 10° C. for 30 minutes, and then at room temperature for 3 hours. The resulting suspension was poured into water (1.2 l) and the oil was extracted into ether. The combined extracts were washed with saturated sodium chloride solution, dried over magnesium sulphate and evaporated to give an orange oil, which was purified by chromatography to give 26.3 g of the desired product as a pale yellow oil.

Workup

  1. waitat room temperature for 3 hours
  2. extractionthe oil was extracted into ether
  3. washThe combined extracts were washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customto give an orange oil, which
  7. customwas purified by chromatography

Sources & evidence

ORD record
ord-48ecee1ddf474e8cbbe0d7537dd578ed
Source dataset
uspto-grants-1992_08
Patent number
US05137564

Reaction notes

Loading…