3-(Trifluoromethyl)phenol → HCID 90403319, compound

HRID 2200658Notes

Reaction equation

HRID 2200658 reaction equation
[CH2:1]([N:8]1[C:16]2[N:15]=[C:14](Cl)[N:13]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[C:12]=2[C:11](=[O:26])[N:10]([CH3:27])[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]([F:39])([F:38])[C:31]1[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.O>[CH2:1]([N:8]1[C:16]2[N:15]=[C:14]([O:37][C:33]3[CH:34]=[CH:35][CH:36]=[C:31]([C:30]([F:38])([F:39])[F:29])[CH:32]=3)[N:13]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[C:12]=2[C:11](=[O:26])[N:10]([CH3:27])[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 90402828HCID 90402828, compound

Product 1

HCID 90403319HCID 90403319, compoundYield 41.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-benzyl-8-chloro-7-(4-chlorobenzyl)-1-methyl-1H-purine-2,6(3H,7H)-dione (60 mg, 0.145 mmol) in DMF (3 mL) was added 3-(trifluoromethyl)phenol (35 mg, 0.215 mmol) followed by potassium carbonate (40 mg, 0.29 mmol). The mixture was stirred at 100° C. for 2 h. The mixture was diluted with ethyl acetate and water, and the phases were separated. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. The give crude product was purified by preparative HPLC to give 3-benzyl-7-(4-chlorobenzyl)-1-methyl-8-(3-(trifluoromethyl)phenoxy)-1H-purine-2,6(3H,7H)-dione (31 mg, 41.7% yield) as white solid. 1H-NMR (CDCl3) δ 7.65(s, 1H), 7.58-7.57(m, 2H), 7.45-7.41(m, 5H), 7.33-7.27(m, 5H), 5.42(s, 2H), 5.09(s, 2H), 3.41(s, 3H). LCMS retention time 3.649 min; LCMS (M+H) 541.

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe give crude product
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-ab573c3ba796408b806581570491ea23
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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