Lawesson's reagent → HCID 54201267, compound

HRID 728588Notes

Reaction equation

HRID 728588 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[S:23]1[CH:27]2[NH:28][C:29](=O)[CH:30]=[CH:31][N:26]2[CH:25]=[CH:24]1>CC#N>[S:23]1[CH:27]2[NH:28][C:29](=[S:10])[CH:30]=[CH:31][N:26]2[CH:25]=[CH:24]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 19788559HCID 19788559, compound

Product 1

HCID 54201267HCID 54201267, compoundYield 121.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Lawesson's reagent (5.26 g.) was added to a boiling solution of 8H-thiazolo[3,2-a]pyrimidin-7-one (4.0 g.) in CH3CN(200 ml.) and the mixture was heated under reflux with stirring for 1.5 h. On cooling silica gel (70-230 mesh, 15 g.) was added and the mixture was evaporated to dryness. The residue was applied to a column of silica gel (300 g.) and eluted with MeOH/CH2Cl2 (5-10% to give 8H-thiazolo[3,2-a]-pyrimidin-7-thione (2.7 g.). Trimethyloxonium tetrafluoroborate (2.0 g.) was added to a stirred suspension of 8H-thiazolo[3,2-a]pyrimidin-7-thione (1.5 g.) in dry CH3CN (50 ml.). After stirring for 2 h, the solution was concentrated to about 20 ml., and with vigorous stirring anhydrous ether (100 ml.) was added to precipitate 7-methylthiothiazolo[3,2-a]-pyrimidinium tetrafluoroborate (1.3 g.), having nmr in d6DMSO:

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperatureOn cooling silica gel (70-230 mesh, 15 g.)
  4. additionwas added
  5. customthe mixture was evaporated to dryness
  6. washeluted with MeOH/CH2Cl2 (5-10%

Sources & evidence

ORD record
ord-38e49a9b8a294ab8ad4af2bdb54a8344
Source dataset
uspto-grants-1991_09
Patent number
US05049558

Reaction notes

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