Dimethyl Sulfate → 2-(3-Chlorophenyl)-2-(4,6-dimethoxypyrimidin-2-yl)propiononitrile

HRID 846539Notes

Reaction equation

HRID 846539 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]([C:13]2[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[N:14]=2)[C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1.S(OC)(O[CH3:27])(=O)=O>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]([C:13]2[N:14]=[C:15]([O:21][CH3:22])[CH:16]=[C:17]([O:19][CH3:20])[N:18]=2)([CH3:27])[C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 19882861(3-Chlorophenyl)(4,6-dimethoxypyrimidin-2-yl)acetonitrile

Product 1

HCID 198828572-(3-Chlorophenyl)-2-(4,6-dimethoxypyrimidin-2-yl)propiononitrileYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.83 g of 80% in oil) was added to a stirred solution of the product of Example 48 (8.0 g) in dimethylformamide at room temperature. Dimethyl sulphate (3.5 g) was then added, and the mixture was stirred at room temperature for 4 hours. The mixture was poured onto water (250 ml), and the oil was extracted into ethyl acetate. The combined extracts were dried over magnesium sulphate, and evaporated to give an orange liquid, which was purified by chromatography to give 5.2 g of the desired product as a white solid, mp 89°-93° C.

Workup

  1. additionThe mixture was poured onto water (250 ml)
  2. extractionthe oil was extracted into ethyl acetate
  3. dry with materialThe combined extracts were dried over magnesium sulphate
  4. customevaporated
  5. customto give an orange liquid, which
  6. customwas purified by chromatography

Sources & evidence

ORD record
ord-21ba1516c79949f5af8729f196399fdc
Source dataset
uspto-grants-1992_08
Patent number
US05137564

Reaction notes

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