Methanol → 2-(2,4-Difluorophenyl)-4-(3-trifluoromethylphenyl)-5-methoxypyrimidine

HRID 1612563Notes

Reaction equation

HRID 1612563 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[C:12](S(C)(=O)=O)=[CH:11][N:10]=1.[CH3:29][O-:30].[Na+].CO>COCCOC>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[C:12]([O:30][CH3:29])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 150368532-(2,4-Difluorophenyl)-4-(3-trifluoromethylphenyl)-5-meth anesulfonylpyrimidine

Product 1

HCID 150368542-(2,4-Difluorophenyl)-4-(3-trifluoromethylphenyl)-5-methoxypyrimidineYield 83.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2.1 g of 2-(2,4-difluorophenyl)-4-(3-trifluoromethylphenyl)-5-methanesulfonylpyrimidine, 0.3 g of sodium methoxide and 20 ml of methanol were added to 120 ml of ethylene glycol dimethyl ether and the resulting mixture was heated under reflux for 5 hours. The solvent was distilled away under reduced pressure. The residue was washed with water and then dried to obtain 1.55 g of 2-(2,4-difluorophenyl)-4-(3-trifluoromethylphenyl)-5-methoxypyrimidine (Compound 77).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. distillationThe solvent was distilled away under reduced pressure
  4. washThe residue was washed with water
  5. customdried

Sources & evidence

ORD record
ord-300575e322fa44e0b649afa494c88f14
Source dataset
uspto-grants-1993_03
Patent number
US05190575

Reaction notes

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