Water → 4-Chloro-6-methoxypyrimidine

HRID 68549Notes

Reaction equation

HRID 68549 reaction equation
[CH3:1][O-:2].[Na+].[Cl:4][C:5]1[CH:10]=[C:9](Cl)[N:8]=[CH:7][N:6]=1.O>CO>[Cl:4][C:5]1[CH:10]=[C:9]([O:2][CH3:1])[N:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 709434,6-DichloropyrimidineHCID 10942334Sodium Methoxide2×

Product 1

HCID 10515094-Chloro-6-methoxypyrimidineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.8 g sodium methanolate was added to 10 g 4,6-dichloropyrimidine in 150 mL MeOH at 0° C. The reaction was warmed up to RT and stirred over night at RT. Then 3.63 g sodium methanolate was added and the reaction was stirred for 3 h. The mixture was treated with water and extracted with EtOAc. The organic layer was dried over magesiumsulfate and evaporated to give 9.7 g 4-chloro-6-methoxy-pyrimidine.

Workup

  1. stirringthe reaction was stirred for 3 h
  2. extractionextracted with EtOAc
  3. customThe organic layer was dried over magesiumsulfate
  4. customevaporated

Sources & evidence

ORD record
ord-624b6fe582e74f83bd05d59ee08c46d5
Source dataset
uspto-grants-2014_09
Patent number
US08822464B2

Reaction notes

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