Trimethylsilylacetylene → HCID 21265575, compound

HRID 566187Notes

Reaction equation

HRID 566187 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([N:11]2[C:16](=[O:17])[C:15]([CH3:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[N:13]([CH3:23])[C:12]2=[O:24])=[C:4]([F:25])[CH:3]=1.[CH3:26][Si:27]([C:30]#[CH:31])([CH3:29])[CH3:28]>C(N(CC)CC)C.[Cu]I>[F:25][C:4]1[CH:3]=[C:2]([C:31]#[C:30][Si:27]([CH3:29])([CH3:28])[CH3:26])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]=1[N:11]1[C:16](=[O:17])[C:15]([CH3:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[N:13]([CH3:23])[C:12]1=[O:24]

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 21265591HCID 21265591, compound

Product 1

HCID 21265575HCID 21265575, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent2×

Procedure

3-(4-Bromo-2-fluoro-5-nitrophenyl)-1,5-dimethyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (12.85 g), trimethylsilylacetylene (5.93 g), a palladium chloride-ditriphenylphosphine complex (1.06 g) and copper(I) iodide (0.302 g) were suspended in triethylamine (210 ml), and the mixture was stirred at room temperature for 5 hours. After the reaction, triethylamine was distilled off under reduced pressure. Ethyl acetate was added thereto, and insolubles were filtered. Then, ethyl acetate was distilled off, and the resulting residue was purified by chromatography on silica gel (ethyl acetate:n-hexane=1:3) to obtain the objective 3-{2-fluoro-5-nitro-4-[2-(trimethylsilyl)-1-ethynyl]phenyl}-1,5-dimethyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (11.63 g).

Workup

  1. distillationwas distilled off under reduced pressure
  2. additionEthyl acetate was added
  3. filtrationinsolubles were filtered
  4. distillationThen, ethyl acetate was distilled off
  5. customthe resulting residue was purified by chromatography on silica gel (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-598ab600644d431192bd9f25cd5e8bdb
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

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