Potassium Carbonate → HCID 53989868, compound

HRID 1814981Notes

Reaction equation

HRID 1814981 reaction equation
[OH:1][C@H:2]([CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[NH:14][C:13]([Br:18])=[N:12][C:11]=2[N:10]([CH3:19])[C:8]1=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH2:27]([O:29][CH2:30]Cl)[CH3:28]>CN(C)C=O>[OH:1][C@H:2]([CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH2:30][O:29][CH2:27][CH3:28])[C:13]([Br:18])=[N:12][C:11]=2[N:10]([CH3:19])[C:8]1=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18523Chloromethyl ethyl etherHCID 53632047HCID 53632047, compound

Product 1

HCID 53989868HCID 53989868, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of (R)-1-(5-hydroxyhexyl)-8-bromo-3-methylxanthine (2.9 g, 8.4 mmol) and potassium carbonate (1.50 g, 10.5 mmol) in dimethylformamide (70 ml) was added chloromethyl ethyl ether (0.83 g), 8.8 mmol). After stirring overnight at room temperature, the mixture was poured into ice cold water (200 ml) and was stirred at 0-5° C. for 1 hour. The precipitate was filtered, rinsed with water (5×25 ml) and dried under vacuum to provide (R)-1-(5-hydroxyhexyl)-8-bromo-7-ethoxymethyl-3-methylxanthine (2.5 g, 74% yield) as a white solid.

Workup

  1. stirringwas stirred at 0-5° C. for 1 hour
  2. filtrationThe precipitate was filtered
  3. washrinsed with water (5×25 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e99d16c1bf284880b14405770639c13c
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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