2-Fluorophenol → HCID 53724169, compound

HRID 976251Notes

Reaction equation

HRID 976251 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][C:8]([O:10][CH3:11])=[O:9])=[C:5]([OH:12])[C:4]([CH3:13])=[N:3]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:21]1[CH:26]=[C:25](Cl)[N:24]=[CH:23][N:22]=1.[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[OH:35]>CN(C)C=O>[CH3:1][N:2]1[C:6]([CH2:7][C:8]([O:10][CH3:11])=[O:9])=[C:5]([O:12][C:21]2[CH:26]=[C:25]([O:35][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[F:28])[N:24]=[CH:23][N:22]=2)[C:4]([CH3:13])=[N:3]1

Participants

6

Reactant 4

HCID 97072-FluorophenolHCID 11430Potassium CarbonateHCID 709434,6-DichloropyrimidineHCID 18974399HCID 18974399, compound

Product 1

HCID 53724169HCID 53724169, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.0 g (16.3 mmol) of methyl (1,3-dimethyl-4-hydroxypyrazol-5-yl)acetate in 80 ml of dimethyl formamide are added 6.9 g (50.0 mmol) of potassium carbonate and 2.7 g (18.0 mmol) of 4,6-dichloropyrimidine. After stirring for 3 hours at room temperature, 2.2 g (20.0 mmol) of 2-fluorophenol are added and stirring is continued for 3 hours at 80°-85° C. Then 300 ml of ice-water are added, followed by extraction with 400 ml of diethyl ether. The organic phase is washed with 2M sodium hydroxide solution, water and sodium chloride solution, dried and concentrated under vacuum. The resultant brown oil is chromatographed over silica gel with tetrahydrofuran/n-hexane (1:1) as eluant, giving methyl {1,3-dimethyl-4-[6-(2-fluorophenoxy)pyrimidin-4-yloxy]pyrazol-5-yl}acetate as a yellow resin: MS: 372 (M+, 80%), 312 (100).

Workup

  1. stirringstirring
  2. waitis continued for 3 hours at 80°-85° C
  3. extractionfollowed by extraction with 400 ml of diethyl ether
  4. washThe organic phase is washed with 2M sodium hydroxide solution, water and sodium chloride solution
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customThe resultant brown oil is chromatographed over silica gel with tetrahydrofuran/n-hexane (1:1) as eluant

Sources & evidence

ORD record
ord-ee888118d7f24a928b11222762cc5b6b
Source dataset
uspto-grants-1997_03
Patent number
US05612338

Reaction notes

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