Water → HCID 53837538, compound

HRID 1814932Notes

Reaction equation

HRID 1814932 reaction equation
[CH3:1][NH2:2].[C:3]([O:6][C@H:7]([CH3:29])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH2:23][O:24][CH2:25][CH3:26])[C:18](Br)=[N:17][C:16]=2[N:15]([CH3:28])[C:13]1=[O:14])(=[O:5])[CH3:4].O>CS(C)=O>[C:3]([O:6][C@H:7]([CH3:29])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH2:23][O:24][CH2:25][CH3:26])[C:18]([NH:2][CH3:1])=[N:17][C:16]=2[N:15]([CH3:28])[C:13]1=[O:14])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 54041337(R)-1-(5-acetoxyhexyl)-8-bromo-7-ethoxymethyl-3-methylxanthine

Product 1

HCID 53837538HCID 53837538, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A 40% aqueous solution of methylamine (10 ml) was added to a solution of (R)-1-(5-acetoxyhexyl)-8-bromo-7-ethoxymethyl-3-methylxanthine (0.450 g) in dimethylsulfoxide (20 ml). After heating at 70° C. for 6 hours, the mixture was treated with water (50 ml) and extracted with ethyl acetate (3x 50 ml). The combined extracts were washed with water (2x 30 ml), dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 10% methanol-ethyl acetate to provide (R)-1-(5-acetoxyhexyl)-7-ethoxymethyl-3-methyl-8-methylaminoxanthine (0.32 g).

Workup

  1. extractionextracted with ethyl acetate (3x 50 ml)
  2. washThe combined extracts were washed with water (2x 30 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel eluting with 10% methanol-ethyl acetate

Sources & evidence

ORD record
ord-19ea49729a4648b9998bec4e41501f83
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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