Trifluoroacetic acid → HCID 86723516, compound

HRID 2201278Notes

Reaction equation

HRID 2201278 reaction equation
[CH3:1][N:2]([CH2:4][C@H:5]([N:27]1[C:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:34]2[C:29]([N:30]([CH3:45])[C:31](=[O:44])[N:32]([CH3:43])[C:33]2=[O:42])=[CH:28]1)[CH2:6][S:7]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:3].C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[CH3:1][N:2]([CH3:3])[CH2:4][C@H:5]([N:27]1[C:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:34]2[C:29]([N:30]([CH3:45])[C:31](=[O:44])[N:32]([CH3:43])[C:33]2=[O:42])=[CH:28]1)[CH2:6][SH:7]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86723515HCID 86723515, compound

Product 1

HCID 86723516HCID 86723516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-((S)-1-Dimethylaminomethyl-2-tritylsulfanyl-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione (step 4) (1.3 g, 2.115 mmol) was dissolved in DCM (50 mL) and TFA (5 mL, 64.9 mmol) and triethylsilane (0.675 mL, 4.23 mmol) were added. The mixture was stirred at RT for 1 hour 20 mins. The reaction mixture was rigorously evaporated under vacuum. Purification by chromatography on silica, eluting with 20-100% EtOAc/hexane, 10% MeOH/EtOAc and 10% (7N NH3 in MeOH)/EtOAc gave the title compound.

Workup

  1. customThe reaction mixture was rigorously evaporated under vacuum
  2. customPurification by chromatography on silica
  3. washeluting with 20-100% EtOAc/hexane, 10% MeOH/EtOAc and 10% (7N NH3 in MeOH)/EtOAc

Sources & evidence

ORD record
ord-12bb2d393443414788e289729900aaf7
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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