Water → HCID 135736655, compound

HRID 358809Notes

Reaction equation

HRID 358809 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[N:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:18][CH:17]=3)=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8]C.O>C(O)(=O)C.Br>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[N:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:18][CH:17]=3)=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 2

HCID 962WaterHCID 14745779HCID 14745779, compound

Product 1

HCID 135736655HCID 135736655, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

2.5 g of the 2-(3-fluoro-4-methoxyphenyl)-5-(4-heptylphenyl)pyrimidine obtained in Example 1 was dissolved in a mixture of 200 ml of acetic acid and 100 ml of 47% hydrobromic acid. The obtained solution was heated under reflux for 18 hours. The reaction mixture was allowed to cool to room temperature and 500 ml of water was added thereto. The crystals thus precipitated were filtered. The product thus obtained was purified by column chromatography (developing solvent: hexane: ethyl acetate 5:1) to thereby give 2.1 g of 2-(3-fluoro-4-hydroxyphenyl)-5-(4-heptylphenyl)pyrimidine. Yield: 87%.

Workup

  1. temperatureThe obtained solution was heated
  2. temperatureunder reflux for 18 hours
  3. customThe crystals thus precipitated
  4. filtrationwere filtered
  5. customThe product thus obtained
  6. customwas purified by column chromatography (developing solvent: hexane: ethyl acetate 5:1)

Sources & evidence

ORD record
ord-4042a832bff84b12917b349155f481f5
Source dataset
uspto-grants-1991_03
Patent number
US04997942

Reaction notes

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