2-Fluorophenol → HCID 22599811, compound

HRID 1759951Notes

Reaction equation

HRID 1759951 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][C:11]#[C:12][CH3:13])[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[OH:27].[Cl-].[NH4+]>CN(C)C=O>[CH2:10]([O:9][C:6]1[C:7]([F:8])=[C:2]([O:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[F:20])[N:3]=[CH:4][N:5]=1)[C:11]#[C:12][CH3:13]

Participants

6

Reactant 4

HCID 97072-FluorophenolHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 225997174-(2-Butynyloxy)-5-fluoro-6-chloropyrimidine

Product 1

HCID 22599811HCID 22599811, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 2 ml of N,N-dimethylformamide were added 0.1 g of 4-chloro-6-(2-butynyloxy)-5-fluoropyrimidine, 0.1 g of potassium carbonate, and 0.07 g of 2-fluorophenol, followed by stirring at 80° C. for 3 hours. The reaction mixture was left for cooling to room temperature and poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.11 g of 4-(2-butynyloxy)-6-(2-fluorophenoxy)-5-fluoropyrimidine (the present compound (183)).

Workup

  1. waitThe reaction mixture was left
  2. temperaturefor cooling to room temperature
  3. extractionwas extracted three times with t-butyl methyl ether
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2232b7f9cbe6454fa399cc3262c1e0d9
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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