Potassium Iodide → 1-(2-Hydroxy-3-phenoxy-propyl)-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine

HRID 227219Notes

Reaction equation

HRID 227219 reaction equation
[O:1]([CH2:8][CH:9]1[CH2:11][O:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[K+].[CH3:14][N:15]1[C:23]2[N:22]=[C:21]([Br:24])[N:20]([CH2:25][C:26]#[C:27][CH3:28])[C:19]=2[C:18](=[O:29])[NH:17][C:16]1=[O:30].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[OH:10][CH:9]([CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:11][N:17]1[C:18](=[O:29])[C:19]2[N:20]([CH2:25][C:26]#[C:27][CH3:28])[C:21]([Br:24])=[N:22][C:23]=2[N:15]([CH3:14])[C:16]1=[O:30]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 31217Phenyl glycidyl etherHCID 210889278-Bromo-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione

Product 1

HCID 688286191-(2-Hydroxy-3-phenoxy-propyl)-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

556 mg of 2-phenoxymethyl-oxirane and 110 mg of potassium iodide are added to a mixture of 1.00 g 3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine and 677 mg of potassium carbonate in 25 ml of N,N-dimethylformamide. The reaction mixture is stirred for approx. eight hours at 120° C. For working up it is diluted with water and extracted with ethyl acetate. The combined extracts are dried over magnesium sulphate, evaporated down and chromatographed through a silica gel column with cyclohexane/ethyl acetate (4:1 to 1:1) as eluant.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts are dried over magnesium sulphate
  3. customevaporated down
  4. customchromatographed through a silica gel column with cyclohexane/ethyl acetate (4:1 to 1:1) as eluant

Sources & evidence

ORD record
ord-835ba3e1e1b24c11afff9eebfbf34bb4
Source dataset
uspto-grants-2009_07
Patent number
US07560450B2

Reaction notes

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