Potassium Carbonate → HCID 21258170, compound

HRID 635206Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH3:20])[C:13](=[O:21])[NH:12][C:11]=2[N:10]=[C:9]1[C:22]([CH3:25])([CH3:24])[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].CS([CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])(=O)=O>CN(C)C=O>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH3:20])[C:13](=[O:21])[N:12]([CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[C:11]=2[N:10]=[C:9]1[C:22]([CH3:24])([CH3:23])[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 95 °C

Procedure

5.0 g (14.7 mmol) of 7-benzyl-8-(tert.-butyl)-1-n-propyl-xanthine are dissolved in 200 ml of dimethylformamide. After the addition of 5.36 g of K2CO3, 19.6 mmol of methyl 3-methanesulphonylpropionate are added at ambient temperature and the mixture is then heated to 90-100° C. After about 20 hours at constant temperature the solvent is distilled off in vacuo and the residue remaining is taken up in dichloromethane. The organic phase is washed with water, dried over MgSO4 and the solvent is distilled off in vacuo. The crude product remaining is purified by chromatography on silica gel (dichloromethane:methanol 97:3).

Workup

additionare added at ambient temperature
distillationAfter about 20 hours at constant temperature the solvent is distilled off in vacuo
washThe organic phase is washed with water
dry with materialdried over MgSO4
distillationthe solvent is distilled off in vacuo
customThe crude product remaining is purified by chromatography on silica gel (dichloromethane:methanol 97:3)

Sources & evidence

ORD record: ord-f13d4f34e21c4543b9b1d3bf8ce5a5f8
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06187780B1

Reaction notes

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