Potassium Carbonate → 1,3-Dipropyl-8-{4-[3-(4-trifluoromethoxy-phenyl)-prop-2-ynyloxy]-phenyl}-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione

HRID 889010Notes

Reaction equation

HRID 889010 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:15]3[C:14](=[O:25])[N:13]([CH2:26][CH2:27][CH3:28])[C:12](=[O:29])[N:11]([CH2:30][CH2:31][CH3:32])[C:10]=3[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:40][C:41]#[C:42][C:43]1[CH:48]=[CH:47][C:46]([O:49][C:50]([F:53])([F:52])[F:51])=[CH:45][CH:44]=1>CC(C)=O>[CH2:26]([N:13]1[C:14](=[O:25])[C:15]2[N:16]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:23])([CH3:22])[CH3:24])[C:8]([C:5]3[CH:4]=[CH:3][C:2]([O:1][CH2:40][C:41]#[C:42][C:43]4[CH:44]=[CH:45][C:46]([O:49][C:50]([F:51])([F:52])[F:53])=[CH:47][CH:48]=4)=[CH:7][CH:6]=3)=[N:9][C:10]=2[N:11]([CH2:30][CH2:31][CH3:32])[C:12]1=[O:29])[CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10779014HCID 10779014, compoundHCID 135617740HCID 135617740, compound

Product 1

HCID 579887691,3-Dipropyl-8-{4-[3-(4-trifluoromethoxy-phenyl)-prop-2-ynyloxy]-phenyl}-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dioneYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 8-(4-hydroxy-phenyl)-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (0.100 g, 0.22 mmol) and potassium carbonate (0.076 g, 0.53 mmol), 1-(3-bromo-prop-1-ynyl)-4-trifluoromethoxy-benzene (prepared as given in example E1) (0.073 g, 0.26 mmol) in acetone (10 ml) was heated at 80° C. for 2 hours. The mixture was cooled to room temperature, filtered and washed with acetone. Solvent was evaporated to obtain a residue which was purified by preparative TLC to obtain 1,3-dipropyl-8-{4-[3-(4-trifluoromethoxy-phenyl)-prop-2-ynyloxy]-phenyl}-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione as a pale yellow solid (0.053 g, 37%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. washwashed with acetone
  4. customSolvent was evaporated
  5. customto obtain a residue which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-3e1e4d4052ea4d03904b21486911d46f
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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