Water → 1-(8-Diethylamino-5-hydroxy-5-methyl-6-octynyl)-3-methyl-7-propylxanthine

HRID 1738789Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]1[C:16]2[N:15]=[CH:14][N:13]([CH2:17][CH2:18][CH3:19])[C:12]=2[C:11](=[O:20])[NH:10][C:9]1=[O:21].Cl[CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:37])([CH3:36])[C:28]#[C:29][CH2:30][N:31]([CH2:34][CH3:35])[CH2:32][CH3:33].O>CN(C)C=O>[CH2:34]([N:31]([CH2:32][CH3:33])[CH2:30][C:29]#[C:28][C:27]([OH:37])([CH3:36])[CH2:26][CH2:25][CH2:24][CH2:23][N:10]1[C:11](=[O:20])[C:12]2[N:13]([CH2:17][CH2:18][CH3:19])[CH:14]=[N:15][C:16]=2[N:8]([CH3:7])[C:9]1=[O:21])[CH3:35]

Participants

Conditions

Temperature: 60 °C

Procedure

2.12 g (15.3 mmol) of potassium carbonate were added to a solution of 2.0 g (9.6 mmol) of 3-methyl-7-propylxanthine in 60 ml of dimethylformamide at 60° C. and the mixture was stirred at 60° C. for one hour. Then 3.07 g (12.5 mmol) of 1-chloro-8-diethylamino-5-hydroxy-5-methyl-6-octyne from stage A1) were added dropwise and the mixture was stirred at 80° C. for 12.5 hours. It was then allowed to cool to room temperature, water was added, and three extractions with tert-butyl methyl ether were carried out. The organic phase was dried over magnesium sulfate, concentrated under reduced pressure and purified by flash chromatography, dichloromethane/methanol=19/1.

Workup

stirringthe mixture was stirred at 80° C. for 12.5 hours
temperatureto cool to room temperature
extractionthree extractions with tert-butyl methyl ether
dry with materialThe organic phase was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
custompurified by flash chromatography, dichloromethane/methanol=19/1

Sources & evidence

ORD record: ord-79781c733c30475783413bc0fcbdeb37
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05965555

Reaction notes

Loading…