Potassium Carbonate → HCID 23588607, compound

HRID 889008Notes

Reaction equation

HRID 889008 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:23][C:22]3[C:21](=[O:24])[N:20]([CH2:25][CH2:26][CH3:27])[C:19](=[O:28])[N:18]([CH2:29][CH2:30][CH3:31])[C:17]=3[N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:38][Si:39]([CH3:46])([CH3:45])[CH2:40][CH2:41][O:42][CH2:43]Cl>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:23]([CH2:43][O:42][CH2:41][CH2:40][Si:39]([CH3:46])([CH3:45])[CH3:38])[C:22]3[C:21](=[O:24])[N:20]([CH2:25][CH2:26][CH3:27])[C:19](=[O:28])[N:18]([CH2:29][CH2:30][CH3:31])[C:17]=3[N:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 219587068-(4-Benzyloxy-phenyl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

Product 1

HCID 23588607HCID 23588607, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-(4-benzyloxy-phenyl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (1.2 g, 2.9 mmol) and potassium carbonate (1.19 g, 8.6 mmol), were taken in DMF (15 ml) and 2-(trimethylsilyl)ethoxymethyl chloride (1.52 ml, 8.6 mmol) was added drop wise at 0° C. and mixture was stirred at room temperature for 20 hours. The mixture was cooled to 10° C. and diluted with water, extracted with ethyl acetate. The organic layer was washed with saturated brine solution and dried over Na2SO4. Solvent was removed and residue obtained was further purified by column chromatography to obtain pure 8-(4-benzyloxy-phenyl)-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (1.12 g, 71%).

Workup

  1. temperatureThe mixture was cooled to 10° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine solution
  4. dry with materialdried over Na2SO4
  5. customSolvent was removed
  6. customresidue obtained
  7. customwas further purified by column chromatography

Sources & evidence

ORD record
ord-f6be5069491c4abba01eaa283d98312d
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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