Water → HCID 54266345, compound

HRID 1608552Notes

Reaction equation

HRID 1608552 reaction equation
[OH2:1].O=O.[O:4]=[C:5]([CH3:30])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[NH:14][C:13]([C:18]34[CH2:25][CH:24]5[CH2:26][CH:20]([CH2:21][CH:22]3[CH2:23]5)[CH2:19]4)=[N:12][C:11]=2[N:10]([CH2:27][CH2:28][CH3:29])[C:8]1=[O:9]>CN(C)C=O.[Pd](Cl)Cl>[O:4]=[C:5]([CH3:30])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[NH:14][C:13]([C:18]34[CH2:25][CH:24]5[CH2:26][CH:20]([CH2:21][CH:22]3[CH2:23]5)[CH2:19]4)=[N:12][C:11]=2[N:10]([CH2:27][CH2:28][CH3:29])[C:8]1=[O:9].[O:1]=[CH:30][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[NH:14][C:13]([C:18]34[CH2:25][CH:24]5[CH2:26][CH:20]([CH2:21][CH:22]3[CH2:23]5)[CH2:19]4)=[N:12][C:11]=2[N:10]([CH2:27][CH2:28][CH3:29])[C:8]1=[O:9]

Participants

7

Reactant 3

HCID 962WaterHCID 977OxygenHCID 54266345HCID 54266345, compound

Product 2

HCID 53816235HCID 53816235, compoundYield 27%HCID 54266345HCID 54266345, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 35.0 mg (0.10 mmol) of Compound J obtained in Reference Example 4 in 3 ml of N,N-dimethylformamide was added dropwise to a mixture of 0.5 ml-N,N-dimethylformamide and 0.5 ml-water containing 3.6 mg (0.02 mmol) of palladium chloride and 2.7 mg (0.02 mmol) of cupric chloride. The reaction mixture was stirred at 50° C. for 2 hours in an oxygen atmosphere, poured into 20 ml of ice water, extracted three times with chloroform. The extracts were washed with water, and with a saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give 10.4 mg (yield 28%) of 1-(2-oxopropyl)-8-(3-tricyclo[3.3.1.03,7 ]nonyl)-3-propylxanthine (Compound 9) and 9.9 mg (yield 27%) of Compound 11, as a white powder.

Workup

  1. extractionextracted three times with chloroform
  2. washThe extracts were washed with water
  3. dry with materialwith a saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9bf4c5bdbf75415d8e1585b08134ad76
Source dataset
uspto-grants-1995_03
Patent number
US05395836

Reaction notes

Loading…