Acetic Anhydride → HCID 15764726, compound

HRID 2226698Notes

Reaction equation

HRID 2226698 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.[C:23](OC(=O)C)(=[O:25])[CH3:24]>S(=O)(=O)(O)O>[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][C:23](=[O:25])[CH3:24])[CH:15]=3)[C:11]([O:21][CH3:22])=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14883712HCID 14883712, compound

Product 1

HCID 15764726HCID 15764726, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

One drop of 96% sulfuric acid was added to a mixture of 1.2 g of 2-(4-fluorophenyl)-4-(3-hydroxyphenyl)-5-methoxypyrimidine and 0.5 g of acetic anhydride, and the resulting mixture was stirred for 20 hours at room temperature. After completion of the reaction, ice-cold water was added to 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 of 2-(4-fluorophenyl)-4-(3-acetoxyphenyl)-5-methoxypyrimidine (Compound 55).

Workup

  1. customAfter completion of the reaction, ice-cold water
  2. additionwas added to 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-fb4f9e238e6c4ee3a49f18b027908119
Source dataset
uspto-grants-1994_09
Patent number
US05349108

Reaction notes

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