Trifluoroacetic acid → HCID 136339895, compound

HRID 81411Notes

Reaction equation

HRID 81411 reaction equation
[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH:16]=[C:15]3[C:10]([N:11](CC4C=CC(OC)=CC=4)[C:12](=[O:19])[N:13]([CH3:18])[C:14]3=[O:17])=[N:9]2)=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:2]=[CH:3][C:4]([CH2:7][N:8]2[CH:16]=[C:15]3[C:10]([NH:11][C:12](=[O:19])[N:13]([CH3:18])[C:14]3=[O:17])=[N:9]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 68507378HCID 68507378, compound

Product 1

HCID 136339895HCID 136339895, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(biphenyl-4-ylmethyl)-7-(4-methoxybenzyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione in CH2Cl2 (90 mL) is added TFA (10 mL) slowly at room temperature, followed by adding trifluoromethanesulfonic acid (4 mL) dropwise. After the reaction mixture is stirred at r.t. for 3 hours, solvent is removed under reduced pressure, and the obtained residue is basified by adding cold pre-diluted ammonium hydroxide (NH3 content, 7%) at 0° C. The mixture is extracted with ethyl acetate four times. The combined organic phase is washed with brine, dried over anhydrous Na2SO4, and then filtered. The filtrate is evaporated to dryness to give crude product in almost quantitative yield. MS (ESI) m/z 333.1 [M+H]+.

Workup

  1. customsolvent is removed under reduced pressure
  2. additionby adding cold pre-diluted ammonium hydroxide (NH3 content, 7%) at 0° C
  3. extractionThe mixture is extracted with ethyl acetate four times
  4. washThe combined organic phase is washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customThe filtrate is evaporated to dryness
  8. customto give crude product in almost quantitative yield

Sources & evidence

ORD record
ord-eba80dccf1a642aa855391726adce802
Source dataset
uspto-grants-2014_09
Patent number
US08846693B2

Reaction notes

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