Trifluoroacetic acid → HCID 90402690, compound

HRID 2200601Notes

Reaction equation

HRID 2200601 reaction equation
COC1C=CC(C[N:8]2[C:16](=[O:17])[C:15]3[N:14]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=4)[C:13]([CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([O:33][C:34]([F:37])([F:36])[F:35])[CH:28]=4)=[N:12][C:11]=3[N:10]([CH3:38])[C:9]2=[O:39])=CC=1.OS(C(F)(F)F)(=O)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:38][N:10]1[C:11]2[N:12]=[C:13]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][C:34]([F:37])([F:36])[F:35])[CH:28]=3)[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)[C:15]=2[C:16](=[O:17])[NH:8][C:9]1=[O:39]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 90402978HCID 90402978, compound

Product 1

HCID 90402690HCID 90402690, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-methoxybenzyl)-3-methyl-7-((5-methylpyridin-2-yl)methyl)-8-(3-(trifluoromethoxy)benzyl)-1H-purine-2,6(3H,7H)-dione (120 mg, 0.212 mmol) in DCM (1.4 mL) was added triflic acid (0.7 mL) and TFA (0.7 mL). The reaction was stirred at room temperature overnight. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with saturated NaHCO3 and brine, dried over sodium sulfate, filtered and concentrated to give crude product, which was purified by silica gel chromatography eluting with petroleum/ethyl acetate (10:1 to 1:1) to give 3-methyl-7-((5-methylpyridin-2-yl)methyl)-8-(3-(trifluoromethoxy)benzyl)-1H-purine-2,6(3H,7H)-dione (60 mg, 63.5% yield) as white solid. LCMS MH+ 446.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with saturated NaHCO3 and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas purified by silica gel chromatography
  8. washeluting with petroleum/ethyl acetate (10:1 to 1:1)

Sources & evidence

ORD record
ord-58c0297747694c4a822a31c988b79ce6
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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