N,N-Dimethylaniline → 4-Chloro-2-methyl-6-(trifluoromethyl)pyrimidine
Reaction equation
[CH3:1][C:2]1[NH:7][C:6](=O)[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:6]1[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=[C:2]([CH3:1])[N:7]=1Participants
4
Procedure
2-Methyl-6-trifluoromethyl-4H-pyrimidin-4-one of Example 4 (2.00 g, 11.2 mmol) was mixed with phosphorus oxychloride (10 mL) and N,N-dimethylaniline (2 mL), and refluxed for 3 h. The dark solution was poured into crushed ice and extracted with Et2O. The organic layer was washed with H2O (twice), dried over Na2SO4, then evaporated to dryness to afford 2.00 g (91%) of an oil.
Workup
- temperaturerefluxed for 3 h
- additionThe dark solution was poured
- custominto crushed ice
- extractionextracted with Et2O
- washThe organic layer was washed with H2O (twice),
- dry with materialdried over Na2SO4
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-d66baf91973745fa92ccb180c08c8bb8
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05336677
Reaction notes
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