Tetrabutylammonium Fluoride → HCID 15610799, compound

HRID 1607554Notes

Reaction equation

HRID 1607554 reaction equation
[CH2:1]([S:8][C:9]1[S:24][C:12]2=[N:13][CH:14]=[C:15]([C:18]#[C:19][Si](C)(C)C)[C:16](=[O:17])[N:11]2[N:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:18]([C:15]1[C:16](=[O:17])[N:11]2[N:10]=[C:9]([S:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[S:24][C:12]2=[N:13][CH:14]=1)#[CH:19]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 15610798HCID 15610798, compound

Product 1

HCID 15610799HCID 15610799, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 100 ml of tetrahydrofurane, 5.4 g of the thus obtained 2-heptylthio-6-trimethylsilylethynyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one, and the solution was cooled to -65° C. in an acetone-dry ice bath. To the cooled solution, a solution of 0.93 g of tetrabutylammonium fluoride in 200 ml of tetrahydrofurane was added dropwise. The solution was stirred at -70~-65° C. for 1 hour. After the solution was brought to room temperature, the solution 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 thus 3.0 g of 6-ethynyl-2-heptylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained.

Workup

  1. customwas brought to room temperature
  2. filtrationthe solution was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e70c0f67aa924453912e46ec16954215
Source dataset
uspto-grants-1989_09
Patent number
US04866064

Reaction notes

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