Trifluoroacetic acid → HCID 86723529, compound

HRID 2201295Notes

Reaction equation

HRID 2201295 reaction equation
[CH2:1]([N:3]1[C:8]2=[CH:9][N:10]([CH2:18][CH2:19][S:20]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:7]2[C:6](=[O:40])[N:5]([CH2:41][CH3:42])[C:4]1=[O:43])[CH3:2].C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([N:3]1[C:8]2=[CH:9][N:10]([CH2:18][CH2:19][SH:20])[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:7]2[C:6](=[O:40])[N:5]([CH2:41][CH3:42])[C:4]1=[O:43])[CH3:2]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 86723527HCID 86723527, compound

Product 1

HCID 86723529HCID 86723529, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3-Diethyl-5-phenyl-6-(2-(tritylthio)ethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (step 4) (1.45 g, 2.475 mmol) was dissolved in DCM (50 mL) and treated with TFA (5 mL, 64.9 mmol) followed by triethylsilane (0.791 mL, 4.95 mmol). The mixture was stirred at RT for 16 h. The reaction mixture was basified by slow addition of sat. NaHCO3(aq) and extracted with DCM. The organic phase was passed through a hydrophobic frit and evaporated under vacuum. The residue was dissolved in DCM, evaporated onto silica and the silica deposited onto a 10 g silica cartridge. The system was eluted with 20%-60% EtOA in iso-hexane to yield the title compound as a pale yellow oil.

Workup

  1. extractionextracted with DCM
  2. customevaporated under vacuum
  3. dissolutionThe residue was dissolved in DCM
  4. customevaporated onto silica
  5. washThe system was eluted with 20%-60% EtOA in iso-hexane

Sources & evidence

ORD record
ord-60145154f231458093251a1be3d092b9
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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