Potassium ethanethioate → (1-((tert-Butyldimethylsilyl)oxy)-3-(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl) ethanethioate

HRID 2201209Notes

Reaction equation

HRID 2201209 reaction equation
CS([O:5][CH:6]([CH2:16][N:17]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)=[C:24]2[C:19]([N:20]([CH3:36])[C:21](=[O:35])[N:22]([CH3:34])[C:23]2=[O:33])=[CH:18]1)[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])(=O)=O.[C:37]([O-])(=[S:39])[CH3:38].[K+]>CN(C=O)C.O>[C:37](=[S:39])([O:5][CH:6]([CH2:16][N:17]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)=[C:24]2[C:19]([N:20]([CH3:36])[C:21](=[O:35])[N:22]([CH3:34])[C:23]2=[O:33])=[CH:18]1)[CH2:7][O:8][Si:9]([C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:10])[CH3:11])[CH3:38]

Participants

5

Reactant 2

HCID 23670855Potassium ethanethioate2×HCID 867234491-((tert-Butyldimethylsilyl)oxy)-3-(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl methanesulfonate

Product 1

HCID 131735715(1-((tert-Butyldimethylsilyl)oxy)-3-(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl) ethanethioate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-((tert-butyldimethylsilyl)oxy)-3-(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl methanesulfonate (705 mg, 1.241 mmol) and potassium thioacetate (709 mg, 6.20 mmol) in DMF (4964 μL) was heated at 70° C. for 4 hours. Further portions of potassium thioacetate (709 mg, 6.20 mmol) were added as necessary to allow the reaction to run to completion. The reaction mixture was cooled to room temperature, diluted with water (15 mL) and extracted with DCM (3×20 mL). The combined organic extracts were dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-50% EtOAc/hexane, afforded the title compound.

Workup

  1. customthe reaction
  2. extractionextracted with DCM (3×20 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. customevaporated under vacuum
  5. customPurification by chromatography on silica
  6. washeluting with 0-50% EtOAc/hexane

Sources & evidence

ORD record
ord-f45e4291253c4d62afeae4edc00fb1fd
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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