Methanesulfonyl chloride → 2-(4-Fluorophenyl)-4-(3-methanesulfonyloxyphenyl)-5-methoxypyrimidine

HRID 326812Notes

Reaction equation

HRID 326812 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]([OH:20])[CH:15]=3)[C:11]([O:21][CH3:22])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][S:24]([CH3:23])(=[O:26])=[O:25])[CH:15]=3)[C:11]([O:21][CH3:22])=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 14883712HCID 14883712, compound

Product 1

HCID 148837572-(4-Fluorophenyl)-4-(3-methanesulfonyloxyphenyl)-5-methoxypyrimidineYield 66%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.2 g of 2-(4-fluorophenyl)-4-(3-hydroxyphenyl)-5-methoxypyrimidine and 0.57 g of methanesulfonyl chloride were added to 10 ml of pyridine, and the resulting mixture was stirred for 3 hours at room temperature. After completion of the reaction, ice-cold water was added to the mixture. Subsequently, the mixture was extracted with ethyl acetate. The solvent was evaporated off, and the residue was purified by column chromatography on silica gel, thereby obtaining 1.0 g 2-(4-fluorophenyl)-4-(3-methanesulfonyloxyphenyl)-5-methoxypyrimidine (Compound 54).

Workup

  1. customAfter completion of the reaction, ice-cold water
  2. additionwas added to the mixture
  3. extractionSubsequently, the mixture was extracted with ethyl acetate
  4. customThe solvent was evaporated off
  5. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d096bf354e3e4377853f7b953a78467c
Source dataset
uspto-grants-1993_12
Patent number
US05270467

Reaction notes

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