Lawesson's reagent → HCID 86658480, compound

HRID 335886Notes

Reaction equation

HRID 335886 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[F:23][C:24]1([F:55])[C:53](=O)[NH:52][C:26]2([C:39]3[CH:38]=[C:37]([O:40][CH2:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH:36]=[CH:35][C:34]=3[O:33][C:32]3[C:27]2=[CH:28][C:29]([C:46]2[CH:47]=[N:48][CH:49]=[N:50][CH:51]=2)=[CH:30][CH:31]=3)[CH2:25]1>C1(C)C=CC=CC=1>[F:23][C:24]1([F:55])[C:53](=[S:10])[NH:52][C:26]2([C:39]3[CH:38]=[C:37]([O:40][CH2:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH:36]=[CH:35][C:34]=3[O:33][C:32]3[C:27]2=[CH:28][C:29]([C:46]2[CH:47]=[N:48][CH:49]=[N:50][CH:51]=2)=[CH:30][CH:31]=3)[CH2:25]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67383470HCID 67383470, compound

Product 1

HCID 86658480HCID 86658480, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Lawesson's reagent (6.72 mg, 0.017 mmol) was added to a solution of 4,4-difluoro-2′-(neopentyloxy)-7′-(pyrimidin-5-yl)spiro[pyrrolidine-2,9′-xanthen]-5-one (0.015 g, 0.033 mmol) in toluene (0.665 mL) and the reaction was heated at 90° C. for 2.5 hours before being concentrated. The crude material was purified by dissolving in a minimal amount of CH2Cl2 and filtering through a pad of silica gel eluting with 1:4 EtOAc in hexane followed by 1:1 EtOAc in hexane, to provide 4,4-difluoro-2′-(neopentyloxy)-7′-(pyrimidin-5-yl)spiro[pyrrolidine-2,9′-xanthene]-5-thione. M=468.1 [M+H].

Workup

  1. concentrationbefore being concentrated
  2. customThe crude material was purified
  3. dissolutionby dissolving in a minimal amount of CH2Cl2
  4. filtrationfiltering through a pad of silica gel eluting with 1:4 EtOAc in hexane

Sources & evidence

ORD record
ord-9fc4b7e328d1479880f73b29683935c4
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

Loading…