Trifluoroacetic acid → (S)-6-(2-Mercaptopropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2201284Notes

Reaction equation

HRID 2201284 reaction equation
[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([CH2:17][C@@H:18]([S:20]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:19])[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:6]2[C:5](=[O:40])[N:4]([CH3:41])[C:3]1=[O:42].C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[SH:20][C@@H:18]([CH3:19])[CH2:17][N:9]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:6]2[C:7]([N:2]([CH3:1])[C:3](=[O:42])[N:4]([CH3:41])[C:5]2=[O:40])=[CH:8]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86723520(S)-1,3-dimethyl-5-phenyl-6-(2-(tritylthio)propyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 86723519(S)-6-(2-Mercaptopropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To crude (S)-1,3-dimethyl-5-phenyl-6-(2-(tritylthio)propyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (step 3)(1.35 mg, 1.06 mmol) in DCM (30 ml) was added TFA (4.09 ml, 53.1 mmol) and triethylsilane (1.7 ml, 10.6 mmol) giving a yellow solution. The mixture was stirred at RT overnight. The reaction mixture was evaporated under vacuum. The residue was partitioned between DCM/water and the phases separated. The organic phase was passed through a hydrophobic frit and evaporated under vacuum. The solid was dissolved in a minimal volume of DCM and purified via ISCO column chromatography, 40 g silica, liquid load, 0-60% iso-hexane:EtOAc, product eluting at 50% affording 7 pure fractions. Corresponding fractions were reduced in vacuo to yield the title compound as a white solid.

Workup

  1. customgiving a yellow solution
  2. customThe reaction mixture was evaporated under vacuum
  3. customThe residue was partitioned between DCM/water
  4. customthe phases separated
  5. customevaporated under vacuum
  6. dissolutionThe solid was dissolved in a minimal volume of DCM
  7. custompurified via ISCO column chromatography, 40 g silica, liquid load, 0-60% iso-hexane
  8. washEtOAc, product eluting at 50%
  9. customaffording 7 pure fractions

Sources & evidence

ORD record
ord-0df99338a3744d3ebb9816d895ed0a5f
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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