Potassium Fluoride → HCID 86756227, compound

HRID 566180Notes

Reaction equation

HRID 566180 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][Si](C)(C)C)[C:5]2[O:6][CH:7]([CH3:9])[CH2:8][C:4]=2[C:3]=1[N:18]1[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([CH3:29])[C:19]1=[O:30].[F-].[K+]>C(O)C>[C:12]([C:10]1[C:5]2[O:6][CH:7]([CH3:9])[CH2:8][C:4]=2[C:3]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([CH3:29])[C:19]2=[O:30])=[C:2]([F:1])[CH:11]=1)#[CH:13]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 70220561HCID 70220561, compound

Product 1

HCID 86756227HCID 86756227, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-{5-Fluoro-2-methyl-7-[2-(trimethylsilyl)-1-ethynyl]-2,3-dihydrobenzo[b]furan-4-yl}-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.39 g) was dissolved in ethanol (4 ml). To this solution, an aqueous solution (0.3 ml) of potassium fluoride (84 mg) was added dropwise at room temperature, and the mixture was stirred for further 8 hours. After the reaction, ethanol was distilled off under reduced pressure, extracted with ethyl acetate, washed with water, and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off and the resulting oily substance was purified by chromatography on silica gel (ethyl acetate:n-hexane=1:3 v/v) to obtain the objective 3-[7-(1-ethynyl)-5-fluoro-2-methyl-2,3-dihydrobenzo[b]furan-4-yl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.26 g).

Workup

  1. distillationwas distilled off under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationEthyl acetate was distilled off
  6. customthe resulting oily substance was purified by chromatography on silica gel (ethyl acetate:n-hexane=1:3 v/v)

Sources & evidence

ORD record
ord-555e233ad22244828a01e6d616faa556
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

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