Water → 7-Benzyl-3-butyl-1-(3-methoxypropyl)xanthine

HRID 323854

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[NH:20][C:19](=[O:24])[N:18]([CH2:25][CH2:26][CH2:27][CH3:28])[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:29][O:30][CH2:31][CH2:32][CH2:33]Cl.O>CN(C)C=O>[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[N:20]([CH2:33][CH2:32][CH2:31][O:30][CH3:29])[C:19](=[O:24])[N:18]([CH2:25][CH2:26][CH2:27][CH3:28])[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2.1 g (15.2 mmol) of potassium carbonate were added to a hot solution of 3 g (10.0 mmol) of 7-benzyl-3-butylxanthine from stage a) in 90 ml of dimethylformamide at 60° C. and the mixture was stirred at 60° C. for one hour. 1.3 g (12.0 mol) of 3-methoxypropyl chloride were then added dropwise and the mixture was stirred at 100° C. for 3 hours. It was then allowed to cool to room temperature, and was treated with water and extracted using dichloromethane. The organic phase was washed with water and 1 N sodium hydroxide solution, dried using sodium sulfate and concentrated under reduced pressure. The oily residue was purified by flash chromatography on a silica gel column, toluene/ethanol (39/1)

Workup

stirringthe mixture was stirred at 100° C. for 3 hours
temperatureto cool to room temperature
extractionextracted
washThe organic phase was washed with water and 1 N sodium hydroxide solution
customdried
concentrationconcentrated under reduced pressure
customThe oily residue was purified by flash chromatography on a silica gel column, toluene/ethanol (39/1)

Sources & evidence

ORD record: ord-c199c823af21472ea9d71f2e27f502ff
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06214992B1

Linked notes

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