Sodium Chloride → HCID 13911463, compound

HRID 1085698Notes

Reaction equation

HRID 1085698 reaction equation
[CH3:1][C:2]([C:5]1[N:10]=[C:9](Cl)[C:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][N:6]=1)([CH3:4])[CH3:3].[OH-].[NH4+].[Cl-].[Na+]>[Zn].C1(C)C=CC=CC=1>[CH3:4][C:2]([C:5]1[N:10]=[CH:9][C:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][N:6]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 14923Ammonium HydroxideHCID 817777HCID 817777, compound

Product 1

HCID 13911463HCID 13911463, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 2-[2-(1,1-dimethylethyl)-4-chloropyrimidin-5-yl]acetate (18 g), toluene (180 cm3), zinc dust (36 g) and 3 molar ammonium hydroxide solution saturated with sodium chloride (180 cm3) was heated at 100° C. for 120 hours. After cooling and filtering to remove the solid component the organic phase was separated, the aqueous phase washed with ethyl acetate and the washings combined with the organic phase. After washing the organic phase with water and drying over anhydrous magnesium sulphate the solvents were removed by evaporation under reduced pressure and the residual oil (16 g) was subjected to purification by column chromatography using a silica column eluted with dichloromethane to yield ethyl 2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]acetate (12 g) as a yellow oil.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltering
  3. customto remove the solid component the organic phase
  4. customwas separated
  5. washthe aqueous phase washed with ethyl acetate
  6. washAfter washing the organic phase with water
  7. dry with materialdrying over anhydrous magnesium sulphate the solvents
  8. customwere removed by evaporation under reduced pressure
  9. customthe residual oil (16 g) was subjected to purification by column chromatography
  10. washeluted with dichloromethane

Sources & evidence

ORD record
ord-78d9bb6eb837406ba199c2cc4f0ee2a7
Source dataset
uspto-grants-1991_04
Patent number
US05010200

Reaction notes

Loading…