Potassium Carbonate → 7-Benzyl-3-cyclopropyl-1-(2-methoxyethyl)xanthine

HRID 323852Notes

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]([CH:25]3[CH2:27][CH2:26]3)[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:28][O:29][CH2:30][CH2:31]Cl>CN(C)C=O>[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[N:20]([CH2:31][CH2:30][O:29][CH3:28])[C:19](=[O:24])[N:18]([CH:25]3[CH2:26][CH2:27]3)[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2.2 g (15.9 mmol) of potassium carbonate were added to a hot solution of 3 g (11.0 mmol) of 7-benzyl-3-cyclopropylxanthine from stage a) in dimethylformamide at 60° C. and the mixture was stirred at 60° C. for one hour. 1.51 g (15.9 mmol) of 2-methoxyethyl chloride were then added dropwise and the mixture was stirred at 80° C. for 6 hours. It was then allowed to cool to room temperature and concentrated under reduced pressure. The oily residue was taken up in dichloromethane and extracted using 1 N sodium hydroxide solution, washed with water until neutral, dried over magnesium sulfate and concentrated under reduced pressure, and the residue was employed in stage c) without further purification.

Workup

stirringthe mixture was stirred at 80° C. for 6 hours
temperatureto cool to room temperature
concentrationconcentrated under reduced pressure
extractionextracted
washwashed with water until neutral,
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customwithout further purification

Sources & evidence

ORD record: ord-cd3c6fa58c06452693b0db6545f8c5e5
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06214992B1

Reaction notes

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