Water → HCID 53837538, compound

HRID 1835719Notes

Reaction equation

HRID 1835719 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 (3×50 ml). The combined extracts were washed with water (2×30 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 (3×50 ml)
  2. washThe combined extracts were washed with water (2×30 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-afca51d0ede2405b8e6ff51b959331e2
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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