Trifluoroacetic acid → HCID 136614171, compound

HRID 1521676Notes

Reaction equation

HRID 1521676 reaction equation
C(O)(C(F)(F)F)=O.[Br:8][C:9]1[CH:36]=[CH:35][C:12]([CH2:13][N:14]2[CH:22]=[C:21]3[C:16]([N:17](CC4C=CC(OC)=CC=4)[C:18](=[O:25])[N:19]([CH3:24])[C:20]3=[O:23])=[N:15]2)=[CH:11][CH:10]=1.C(S(O)(=O)=O)(F)(F)F>C(Cl)Cl>[Br:8][C:9]1[CH:36]=[CH:35][C:12]([CH2:13][N:14]2[CH:22]=[C:21]3[C:16]([NH:17][C:18](=[O:25])[N:19]([CH3:24])[C:20]3=[O:23])=[N:15]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 90409975HCID 90409975, compound

Product 1

HCID 136614171HCID 136614171, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (500 mL) is slowly added into a suspension of 2-(4-bromobenzyl)-7-(4-methoxybenzyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (226 g, 496 mmol) in methylene chloride (320 mL), and then TFMSA (160 mL) is added slowly. The reaction mixture is stirred at room temperature overnight. Solvents are removed under reduced pressure. The obtained residue is treated with water (4 L) and ethyl acetate (2 L), stirred at room temperature for 30 min, and then filtered. The filter cake is thoroughly washed with water to remove residual acids, followed by washing with ethyl acetate. The obtained white solids are dried in a heated oven to give 159 g of product (yield: 96%). MS (ESI) m/z 335.0 [M+H]+.

Workup

  1. customSolvents are removed under reduced pressure
  2. additionThe obtained residue is treated with water (4 L) and ethyl acetate (2 L)
  3. stirringstirred at room temperature for 30 min
  4. filtrationfiltered
  5. washThe filter cake is thoroughly washed with water
  6. customto remove residual acids
  7. washby washing with ethyl acetate
  8. customThe obtained white solids are dried in a heated oven

Sources & evidence

ORD record
ord-8c603d8c664d4f53a771b0f3aaee9dde
Source dataset
uspto-grants-2015_07
Patent number
US09073936B2

Reaction notes

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