Potassium Carbonate → Xanthine

HRID 2200728Notes

Reaction equation

HRID 2200728 reaction equation
ClC1C=CC(C[N:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12](=[O:17])[N:11](C)[C:10]=3[N:9]=[C:8]2OC2C=CC=C(OC(F)(F)F)C=2)=CC=1.C(=O)([O-])[O-].[K+].[K+].BrCCCO[Si](C(C)(C)C)(C)C>CN(C=O)C.O>[NH:13]1[C:14](=[O:16])[C:15]2[NH:7][CH:8]=[N:9][C:10]=2[NH:11][C:12]1=[O:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 90403003HCID 90403003, compound

Product 1

HCID 1188Xanthine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Step 1 7-(4-chlorobenzyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-2,6(3H,7H)-dione (3.73 g, 7.99 mmol, intermediate 9) and potassium carbonate (1.66 g, 11.99 mmol) were combined in DMF (56 mL) and (3-bromopropoxy)(tert-butyl)dimethylsilane (2.43 g, 9.59 mmol) was added. The reaction was heated at 100° C. After heating for 3 h the reaction was cooled, diluted with water (200 mL) and extracted with ethyl acetate (3×200 ml). The combined extracts were washed with 1N lithium chloride (2×100 mL), dried with magnesium sulfate and evaporated under reduced pressure to provide 1-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-3-methyl-8-(3-trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (5.7 g crude) as a light golden oil. LCMS retention time=5.646 and 98% purity, LCMS MH+ 639.

Workup

  1. temperatureAfter heating for 3 h the reaction
  2. temperaturewas cooled
  3. extractionextracted with ethyl acetate (3×200 ml)
  4. washThe combined extracts were washed with 1N lithium chloride (2×100 mL)
  5. dry with materialdried with magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d3c0e0dadeb34b88aa42730f85948c4d
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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