Trimethylsilylacetylene → 2-benzylthio-7-trimethylsilylethynyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 703837Notes

Reaction equation

HRID 703837 reaction equation
[CH2:1]([S:8][C:9]1[S:19][C:12]2=[N:13][C:14](I)=[CH:15][C:16](=[O:17])[N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([Si:22]([CH3:25])([CH3:24])[CH3:23])#[CH:21]>C(N(CC)CC)C.O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:1]([S:8][C:9]1[S:19][C:12]2=[N:13][C:14]([C:21]#[C:20][Si:22]([CH3:25])([CH3:24])[CH3:23])=[CH:15][C:16](=[O:17])[N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 142544252-benzylthio-7-iodo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 142544262-benzylthio-7-trimethylsilylethynyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent2×

Procedure

In a mixture of 30 ml of triethylamine and 60 ml of tetrahydrofurane, 7.0 g of the thus obtained 55% pure 2-benzylthio-7-iodo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was dissolved, and 0.68 g of bis(triphenylphosphine)palladium (II) chloride and 0.18 g of cuprous iodide were added to the solution. A solution of 3.8 g of ethynyltrimethylsilane in 20 ml of triethylamine was added dropwise to the above solution, the resulting solution was heated to 68°-70° C. and stirred for 4 hours. After cooling, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was separated by silica gel column chromatography using an ethyl acetate/hexane mixture as an eluent, and thus 4.2 g of 2-benzylthio-7-trimethylsilylethynyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained.

Workup

  1. dissolutionwas dissolved
  2. temperaturethe resulting solution was heated to 68°-70° C.
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-0c9ae00be8834ae59404bf4d6e76f8d5
Source dataset
uspto-grants-1991_01
Patent number
US04985432

Reaction notes

Loading…