2-Bromobutane → HCID 14883755, compound

HRID 2226697Notes

Reaction equation

HRID 2226697 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(=O)([O-])[O-].[K+].[K+].Br[CH:30]([CH2:32][CH3:33])[CH3:31]>CC(C)=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][CH:30]([CH2:32][CH3:33])[CH3:31])[CH:15]=3)[C:11]([O:21][CH3:22])=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 65542-BromobutaneHCID 11430Potassium CarbonateHCID 14883712HCID 14883712, compound

Product 1

HCID 14883755HCID 14883755, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.2 g of 2-(4-fluorophenyl)-4-(3-hydroxyphenyl)-5-methoxypyrimidine, 5.5 g of potassium carbonate, and 5.5 g of 2-bromobutane were added to 200 ml of acetone, and the resulting mixture was heated under reflux for 2 days. The solvent was distilled away under reduced pressure. The residue was washed with water, and then purified by column chromatography on silica gel, thereby obtaining 1.0 g of 2-(4-fluorophenyl )-4-[3-sec-butoxyphenyl)-5-methoxypyrimidine (Compound 50).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 days
  3. distillationThe solvent was distilled away under reduced pressure
  4. washThe residue was washed with water
  5. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c0170a4932f54c638801de04cb67cc42
Source dataset
uspto-grants-1994_09
Patent number
US05349108

Reaction notes

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