Sodium Methoxide → 2-(4-Fluorophenyl)-4-(3-trifluoromethylphenyl)-5-methanesulfonylpyrimidine

HRID 2226700Notes

Reaction equation

HRID 2226700 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[C:6]([C:8]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9]N(C)C)=O.Cl.[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[NH:29])=[CH:26][CH:25]=1.C[O-].[Na+]>CO>[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]2[N:30]=[C:6]([C:5]3[CH:17]=[CH:18][CH:19]=[C:3]([C:2]([F:1])([F:20])[F:21])[CH:4]=3)[C:8]([S:13]([CH3:16])(=[O:14])=[O:15])=[CH:9][N:29]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 124561604-Fluorobenzamidine HydrochlorideHCID 541640061-(3-trifluoromethylbenzoyl)-1-methanesulfonyl-2-(N,N-dimethylamino)ethene

Product 1

HCID 148836702-(4-Fluorophenyl)-4-(3-trifluoromethylphenyl)-5-methanesulfonylpyrimidineYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6 g of 1-(3-trifluoromethylbenzoyl)-1-methanesulfonyl-2-(N,N-dimethylamino)ethene and 4 g of 4-fluorobenzamidine hydrochloride were dissolved in 30 ml of methanol at room temperature. After adding 1.2 of sodium methoxide thereto, the mixture was heated under reflux for 1 hour. The solvent was distilled away under reduced pressure. The residue was washed with water, and then dried to obtain 6 g of 2-(4-fluorophenyl)-4-(3-trifluoromethylphenyl)-5-methanesulfonylpyrimidine (Compound 112).

Workup

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

Sources & evidence

ORD record
ord-6e8a5e924733478e9da018705575c020
Source dataset
uspto-grants-1994_09
Patent number
US05349108

Reaction notes

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