Methanol → 2-(4-Fluorophenyl)-4-(3-trifluoromethylphenyl)-5-methoxypyrimidine

HRID 326811Notes

Reaction equation

HRID 326811 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[C:11](S(C)(=O)=O)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:28][O-:29].[Na+].CO>COCCOC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[C:11]([O:29][CH3:28])=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 148836702-(4-Fluorophenyl)-4-(3-trifluoromethylphenyl)-5-methanesulfonylpyrimidine

Product 1

HCID 117253022-(4-Fluorophenyl)-4-(3-trifluoromethylphenyl)-5-methoxypyrimidineYield 85.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2 g of 2-(4-fluorophenyl)-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 1.5 g of 2-(4-fluorophenyl)-4-(3-trifluoromethylphenyl)-5-methoxypyrimidine (Compound 18).

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-a1582ad8349749fab13fbecf2389449c
Source dataset
uspto-grants-1993_12
Patent number
US05270467

Reaction notes

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