Potassium Carbonate → HCID 90402694, compound

HRID 2200607Notes

Reaction equation

HRID 2200607 reaction equation
Br[C:2]1[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:9]2[C:8](=[O:19])[N:7]([CH2:20][CH2:21][CH:22]([OH:24])[CH3:23])[C:6](=[O:25])[N:5]([CH3:26])[C:4]=2[N:3]=1.[F:27][C:28]([F:38])([F:37])[O:29][C:30]1[CH:31]=[C:32]([OH:36])[CH:33]=[CH:34][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[OH:24][CH:22]([CH3:23])[CH2:21][CH2:20][N:7]1[C:8](=[O:19])[C:9]2[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:2]([O:36][C:32]3[CH:33]=[CH:34][CH:35]=[C:30]([O:29][C:28]([F:27])([F:37])[F:38])[CH:31]=3)=[N:3][C:4]=2[N:5]([CH3:26])[C:6]1=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27332613-(Trifluoromethoxy)phenolHCID 90403190HCID 90403190, compound

Product 1

HCID 90402694HCID 90402694, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-bromo-1-(3-hydroxybutyl)-3-methyl-7-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione (1 g, 2.2 mmol) in DNF (10 mL) was added 3-(trifluoromethoxy)phenol (0.6 g, 3 mmol) followed by potassium carbonate (0.6 g, 4.4 mmol). The reaction was stirred at 80° C. for 4 h. The mixture was diluted with ethyl acetate and washed with brine. The organic phase was dried and concentrated to give 1-(3-hydroxybutyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione (1.1 g, 91.8% yield) as yellow syrup. LCMS retention time 2.036 min; LCMS MH+ 545.

Workup

  1. washwashed with brine
  2. customThe organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d042af35bb0a41cf877b9eb15ac9dff4
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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