Trifluoroacetic acid → HCID 86723416, compound

HRID 2201273Notes

Reaction equation

HRID 2201273 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][N:9]1[C:14]2=[CH:15][N:16]([CH2:24][CH2:25][S:26]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:13]2[C:12](=[O:46])[N:11]([CH3:47])[C:10]1=[O:48].C([SiH](CC)CC)C>C(Cl)Cl>[SH:26][CH2:25][CH2:24][N:16]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:13]2[C:14]([N:9]([CH3:8])[C:10](=[O:48])[N:11]([CH3:47])[C:12]2=[O:46])=[CH:15]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86723512HCID 86723512, compound

Product 1

HCID 86723416HCID 86723416, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (5.975 ml, 78 mmol) was added to a solution of 1,3-dimethyl-5-phenyl-6-(2-tritylsulfanyl-ethyl)-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione (step 1) (865 mg, 1.551 mmol) and triethylsilane (2.477 ml, 15.51 mmol) in DCM (20 ml) and the mixture stirred at RT for 3 hours. The solvent was evaporated under reduced pressure. The residue was partitioned between DCM (10 mL) and sat. NaHCO3 (10 mL) and the phases separated. The organic phase was dried over magnesium sulfate and the solvent evaporated under reduced pressure. The residue was triturated with diethyl ether and the solid collected by filtration. The title compound was obtained as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was partitioned between DCM (10 mL) and sat. NaHCO3 (10 mL)
  3. customthe phases separated
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was triturated with diethyl ether
  7. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-34ab087acd7d418dba493f661ba8ccca
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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