Dimethyl Sulfate → HCID 15342491, compound

HRID 341817Notes

Reaction equation

HRID 341817 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[S:10][CH:9]=2)=[CH:3][CH:2]=1.[H-].[Na+].S(OC)(O[CH3:23])(=O)=O>CN(C)C=O>[CH3:23][N:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)[C:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[S:10][CH:9]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 15342490HCID 15342490, compound

Product 1

HCID 15342491HCID 15342491, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 3-(4-pyridinylamino)thieno[2,3-b]pyridine (4 g) in 25 mL of dimethylformamide was added to an ice-cooled suspension of sodium hydride (60% oil dispersion, 0.85 g, washed with heptane) in 5 mL of dimethylformamide. After anion formation was completed a solution of dimethyl sulfate (2.4 g) in 5 mL of dimethylformamide was added. After one hour the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride, and then was dried (anhydrous magnesium sulfate), filtered and evaporated to 4 g of a solid. Elution through silica with 10% methanol in ethyl acetate via flash column chromatography afforded 3 g of a solid, m.p. 143°-145° C. Recrystallization from acetonitrile afforded 2.1 g of crystals, m.p. 150°-152° C.

Workup

  1. temperaturecooled
  2. additionwas added
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water and saturated sodium chloride
  6. dry with materialwas dried (anhydrous magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated to 4 g of a solid
  9. washElution through silica with 10% methanol in ethyl acetate via flash column chromatography

Sources & evidence

ORD record
ord-b8e1726cf2ae49d599314a9c6fdc327c
Source dataset
uspto-grants-1999_01
Patent number
US05856335

Reaction notes

Loading…