Trimethylsilylacetylene → HCID 70220561, compound

HRID 566181Notes

Reaction equation

HRID 566181 reaction equation
Br[C:2]1[C:7]2[O:8][CH:9]([CH3:11])[CH2:10][C:6]=2[C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]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.CN(C=O)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]2[O:8][CH:9]([CH3:11])[CH2:10][C:6]=2[C:5]=1[N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[N:14]([CH3:23])[C:13]1=[O:24]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 21265540HCID 21265540, compound

Product 1

HCID 70220561HCID 70220561, compoundYield 33.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent2×

Procedure

3-(7-Bromo-5-fluoro-2-methyl-2,3-dihydrobenzo[b]furan-4-yl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (1.15 g), trimethylsilylacetylene (0.53 g), a palladium chloride-ditriphenylphosphine complex (95 mg) and copper(I) iodide (27 mg) was suspended in triethylamine (11 ml) and DMF (3 ml), and the mixture was stirred at 50° C. for 12 hours. After the reaction, triethylamine was distilled off under reduced pressure. Ethyl acetate was added thereto, and the 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 v/v) to obtain the objective 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 (0.40 g).

Workup

  1. distillationwas distilled off under reduced pressure
  2. additionEthyl acetate was added
  3. filtrationthe insolubles 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 v/v)

Sources & evidence

ORD record
ord-eceaa87879384386aed24bfb954e782d
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

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