Trimethylsilylacetylene → HCID 15610798, compound

HRID 1607553Notes

Reaction equation

HRID 1607553 reaction equation
[CH2:1]([S:8][C:9]1[S:19][C:12]2=[N:13][CH:14]=[C:15](I)[C:16](=[O:17])[N:11]2[N:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:20]([Si:22]([CH3:25])([CH3:24])[CH3:23])#[CH:21]>C(N(CC)CC)C.O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([S:8][C:9]1[S:19][C:12]2=[N:13][CH:14]=[C:15]([C:21]#[C:20][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:16](=[O:17])[N:11]2[N:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 2

HCID 66111Trimethylsilylacetylene2×HCID 15610797HCID 15610797, compound

Product 1

HCID 15610798HCID 15610798, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent2×

Procedure

In a mixture of 50 ml of triethylamine and 100 ml of tetrahydrofurane, 8.0 g of the thus obtained 2-heptylthio-6-iodo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was dissolved. To this solution, 0.68 g of bis(triphenylphosphine)palladium(II) chloride and 0.2 g of cuprous iodide were added as catalysts. To this mixture, a solution of 3.9 g of ethynyltrimethylsilane in 20 ml of triethylamine was added dropwise. The mixture was warmed to 60°~80° C. and stirred for 1 hour. Thereafter, further the same amounts as above of the catalysts and ethynyltrimethylsilane were added, and the mixture was stirred at 60°~70° C. for 3 hours. After cooling, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using an ethyl acetate/toluene mixture as an eluent, and 5.9 g of 2-heptylthio-6-trimethylsilylethynyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained.

Workup

  1. dissolutionwas dissolved
  2. temperatureThe mixture was warmed to 60°~80° C.
  3. stirringthe mixture was stirred at 60°~70° C. for 3 hours
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9d4c97441ed84f55b33d7379c5263181
Source dataset
uspto-grants-1989_09
Patent number
US04866064

Reaction notes

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