Methanol → 4-Chloro-2,6-dimethoxypyrimidine

HRID 1429177Notes

Reaction equation

HRID 1429177 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH3:10][O-:11].[Na+].[CH3:13][OH:14]>>[Cl:9][C:4]1[CH:5]=[C:6]([O:11][CH3:10])[N:7]=[C:2]([O:14][CH3:13])[N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 773782,4,6-TrichloropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 806004-Chloro-2,6-dimethoxypyrimidineYield 95%

Conditions

Temperature
5 °C

Procedure

2.4.6-Trichloropyrimidin (5.5 g, 30 mmol) was added at once to an ice cooled solution of sodium methoxide (3.3 g, 60 mmol) in methanol (120 ml). The mixture was stirred for one hour at about 5° C. and for two hours at room temperature. The solvent was removed under reduced pressure, water was added and the product was extracted three times with ethyl acetate. The combined organic phases were washed with water, dried with sodium sulphate and evaporated which gave the title compound (5.0 g, 95%), purity about 85%

Workup

  1. customThe solvent was removed under reduced pressure, water
  2. additionwas added
  3. extractionthe product was extracted three times with ethyl acetate
  4. washThe combined organic phases were washed with water
  5. dry with materialdried with sodium sulphate
  6. customevaporated which

Sources & evidence

ORD record
ord-2d860a60971d44c48afc6496340a97e9
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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