Trifluoroacetic acid → HCID 86723445, compound

HRID 2201203Notes

Reaction equation

HRID 2201203 reaction equation
C(=O)([S:3][CH:4]([CH2:14][N:15]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:22]2[C:17]([N:18]([CH3:33])[C:19](=[O:32])[N:20]([CH3:31])[C:21]2=[O:30])=[CH:16]1)[CH2:5][O:6][Si](C(C)(C)C)(C)C)C.[BH4-].[Na+].C(O)(C(F)(F)F)=O>CCO.O.C(Cl)Cl>[OH:6][CH2:5][CH:4]([SH:3])[CH2:14][N:15]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:22]2[C:17]([N:18]([CH3:33])[C:19](=[O:32])[N:20]([CH3:31])[C:21]2=[O:30])=[CH:16]1

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 90218191HCID 90218191, compound

Product 1

HCID 86723445HCID 86723445, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of S-(1-((tert-butyldimethylsilyl)oxy)-3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl) ethanethioate (step 4) (1.62 g, 3.23 mmol) in EtOH (25 ml) was added sodium borohydride (0.61 g, 16.14 mmol) at 0° C. and the solution stirred overnight at RT. The reaction mixture was added slowly to TFA in water (20 ml, 50%). The resulting solid was removed by filtration and the filtrate was concentrated in vacuo to remove EtOH. The resulting mixture was diluted with water and extracted with DCM (×3). The combined organic extracts were passed through a hydrophobic frit and concentrated under reduced pressure to afford an oil. The oil was dissolved in a minimal volume of DCM and purified via ISCO column chromatography, 12 g, liquid load, 0-90% EtOAc in iso-hexane to afford the title compound;

Workup

  1. customThe resulting solid was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto remove EtOH
  4. additionThe resulting mixture was diluted with water
  5. extractionextracted with DCM (×3)
  6. concentrationconcentrated under reduced pressure
  7. customto afford an oil
  8. custompurified via ISCO column chromatography, 12 g, liquid load, 0-90% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-10d713a144a84e06986e473b56e8ef16
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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