Tetrabutylammonium Fluoride → HCID 15610799, compound

HRID 1073797Notes

Reaction equation

HRID 1073797 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. m.p. 140°~142° C. Yield 70%.

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-db8b21734b2a45a2bb3771c864a351b4
Source dataset
uspto-grants-1990_11
Patent number
US04971971

Reaction notes

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