Potassium Carbonate → HCID 90402707, compound

HRID 2200749Notes

Reaction equation

HRID 2200749 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C:13](=[O:29])[N:12]([CH3:30])[C:11]=2[N:10]=[C:9]1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][C:40]=1[C:46]([F:49])([F:48])[F:47]>CN(C=O)C.O>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C:13](=[O:29])[N:12]([CH3:30])[C:11]=2[N:10]=[C:9]1[O:45][C:42]1[CH:43]=[CH:44][C:39]([F:38])=[C:40]([C:46]([F:49])([F:47])[F:48])[CH:41]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6018544-Fluoro-3-(trifluoromethyl)phenolHCID 90402849HCID 90402849, compound2×

Product 1

HCID 90402707HCID 90402707, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Step 1 7-Benzyl-8-bromo-1-(3-((tert-butyldimethylsilyl)oxy)propyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.50 g, 0.985 mmol, intermediate 83), potassium carbonate (0.272 g, 1.97 mmol) and 4-fluoro-3-(trifluoromethyl)phenol (0.19 g, 1.03 mmol) were combined in DMF (5 mL). The reaction was heated at 90° C. After 6 h the reaction was cooled, diluted with water (100 mL) and extracted with ethyl acetate (3×75 mL). The combined extracts were dried with magnesium sulfate, filtered and the solvent was removed under reduced pressure to yield a white solid. This solid was purified using a 25 g silica column eluted with 20% ethyl acetate/hexanes to give 7-benzyl-1-(3-((tert-butyldimethylsilyl)oxy)propyl)-8-(4-fluoro-3-(trifluoromethyl)phenoxy)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.54 g, 90% yield) as a white solid. LCMS retention time=5.342 min and 97% purity, LCMS MH+=607.

Workup

  1. temperatureAfter 6 h the reaction was cooled
  2. extractionextracted with ethyl acetate (3×75 mL)
  3. dry with materialThe combined extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customto yield a white solid
  7. customThis solid was purified
  8. washeluted with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e403da4e22ca45df9cf8dfd4faf40752
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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