Sodium Chloride → HCID 13911463, compound

HRID 34595Notes

Reaction equation

HRID 34595 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][N:5]=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[N:3]=1.[OH-].[NH4+].[Cl-].[Na+]>[Zn].C1(C)C=CC=CC=1>[CH2:12]([O:11][C:9]([CH2:8][C:7]1[CH:2]=[N:3][C:4]([C:14]([CH3:15])([CH3:17])[CH3:16])=[N:5][CH:6]=1)=[O:10])[CH3:13]

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

Procedure

A mixture 4-chloro-5-ethoxycarbonylmethyl-2-(2-methylprop-2-yl)pyrimidine (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 5-ethoxycarbonylmethyl-2-(2-methylprop-2-yl)pyrimidine (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-d2f35e79f3de4514a7f2fcb343708ad3
Source dataset
uspto-grants-1988_08
Patent number
US04762835

Reaction notes

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