Trifluoroacetic acid → HCID 178481638, compound

HRID 72691

Reaction equation

HRID 72691 reaction equation
COC1C=CC(C[N:8]2[C:13]3[NH:14][N:15]=[C:16]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:12]=3[C:11](=[O:24])[N:10]([CH3:25])[C:9]2=[O:26])=CC=1.C(O)(C(F)(F)F)=O.FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[CH3:25][N:10]1[C:11](=[O:24])[C:12]2[C:16]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:15][NH:14][C:13]=2[NH:8][C:9]1=[O:26]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 178490875HCID 178490875, compound

Product 1

HCID 178481638HCID 178481638, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(4-Methoxybenzyl)-5-methyl-3-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (6.6 g, 17.5 mmol) in CH2Cl2 (200 mL) is added TFA (30 mL) slowly at room temperature, followed by adding trifluoromethanesulfonic acid (10 mL) dropwise. After the reaction-mixture is stirred at r.t. for 2 hours, solvent is removed under reduced pressure, and then 200 mL of 1N NaOH is added with cooling. The mixture is extracted with ethyl acetate five times, dried over Na2SO4, and then filtered. The filtrate is evaporated to dryness to give 4.3 g of crude product as white solids (Yield: 96%). MS (ESI) m/z 258.1 [M+H]+.

Workup

  1. customsolvent is removed under reduced pressure
  2. addition200 mL of 1N NaOH is added
  3. temperaturewith cooling
  4. extractionThe mixture is extracted with ethyl acetate five times
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-a704007e81294b31bd1b4c2c7307d379
Source dataset
uspto-grants-2014_09
Patent number
US08829008B2

Linked notes

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