2,4-Dichloropyrimidine → 2-Chloro-4-methoxypyrimidine

HRID 589554Notes

Reaction equation

HRID 589554 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH3:9][O-:10].[Na+]>CO.CCCCCC>[Cl:1][C:2]1[N:7]=[C:6]([O:10][CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Procedure

To a solution of 2,4-dichloro pyrimidine (20 gm) in methanol (200 ml) was added sodium methoxide (8.7 gm) at 0 to 5° C. The resulting mixture was stirred for 14 hours at room temperature and then concentrated under reduced pressure to obtain a residual mass. The residual mass obtained was extracted with ethyl acetate and water. The combined organic layers were washed with water and sodium chloride solution, and then concentrated under vacuum to obtain a crude solid. The crude solid obtained was dissolved in hexane (40 ml) at 0 to 5° C. and stirred for 1 hour. The solid obtained was collected by filtration and then dried to obtain 9.7 gm of 2-chloro-4-methoxypyrimidine.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto obtain a residual mass
  3. customThe residual mass obtained
  4. extractionwas extracted with ethyl acetate and water
  5. washThe combined organic layers were washed with water and sodium chloride solution
  6. concentrationconcentrated under vacuum
  7. customto obtain a crude solid
  8. customThe crude solid obtained
  9. stirringstirred for 1 hour
  10. customThe solid obtained
  11. filtrationwas collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-0a852f52b30b4a3b896ed2d7e61870b4
Source dataset
uspto-grants-2016_01
Patent number
US09233935B2

Reaction notes

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