Potassium Carbonate → HCID 22599730, compound

HRID 1592232Notes

Reaction equation

HRID 1592232 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]=[C:23]([F:27])[C:22]=1[OH:28].[Cl-].[NH4+]>CN(C)C=O>[CH2:10]([O:9][C:6]1[C:7]([F:8])=[C:2]([O:28][C:22]2[C:21]([F:20])=[CH:26][CH:25]=[CH:24][C:23]=2[F:27])[N:3]=[CH:4][N:5]=1)[C:11]#[C:12][CH3:13]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 943922,6-DifluorophenolHCID 225997174-(2-Butynyloxy)-5-fluoro-6-chloropyrimidine

Product 1

HCID 22599730HCID 22599730, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °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 0.08 g of 2,6-difluorophenol, followed by stirring at 60° C. for 4 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 0.1 g of 4-(2-butynyloxy)-6-(2,6-difluorophenoxy)-5-fluoropyrimidine (the present compound (190)).

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-10404908fb9d45bab691ae2e41755158
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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