2,4-Dichloropyrimidine → 2-Chloro-4-methoxypyrimidine
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]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- concentrationconcentrated under reduced pressure
- customto obtain a residual mass
- customThe residual mass obtained
- extractionwas extracted with ethyl acetate and water
- washThe combined organic layers were washed with water and sodium chloride solution
- concentrationconcentrated under vacuum
- customto obtain a crude solid
- customThe crude solid obtained
- stirringstirred for 1 hour
- customThe solid obtained
- filtrationwas collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-0a852f52b30b4a3b896ed2d7e61870b4
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09233935B2
Reaction notes
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