4,6-Dichloropyrimidine → 4-CHLORO-6-ISOPROPOXYPYRIMIDINE

HRID 1979933Notes

Reaction equation

HRID 1979933 reaction equation
[CH3:1][CH:2]([CH3:4])[O-:3].[Na+].[Cl:6][C:7]1[CH:12]=[C:11](Cl)[N:10]=[CH:9][N:8]=1>C(O)(C)C>[Cl:6][C:7]1[CH:12]=[C:11]([O:3][CH:2]([CH3:4])[CH3:1])[N:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 709434,6-DichloropyrimidineHCID 109204432-Propanol, sodium salt (1:1)

Product 1

HCID 116224164-CHLORO-6-ISOPROPOXYPYRIMIDINEYield 271.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of sodium isopropoxide (prepared from 0.77 g sodium) in isopropanol (230 ml) was added dropwise over 8 hours to a stirred solution of 4,6-dichloropyrimidine (5.0 g) in isopropanol (60 ml) at room temperature. The solvent was evaporated in vacuo, the residue taken up in water and extracted three times with diethylether (3×70 ml). The combined ether extracts were dried (Na2SO4) and evaporated in vacuo to give 4-chloro-6-isopropoxy pyrimidine (4.4 g) as an oil, characterized spectroscopically, and used directly.

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionextracted three times with diethylether (3×70 ml)
  3. dry with materialThe combined ether extracts were dried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-95f6fb725c2a423cb4129f8964c0cacd
Source dataset
uspto-grants-1984_11
Patent number
US04483857

Reaction notes

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