Hydrochloric Acid → HCID 15886850, compound
Reaction equation
CC(C)([O-])C.[K+].[NH2:7][C:8]1[N:13]([CH2:14][CH3:15])[C:12](=[O:16])[NH:11][C:10](=[O:17])[C:9]=1[NH:18][C:19](=O)[CH:20]([CH3:22])[CH3:21].[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1.C(Cl)C1C=CC=CC=1.Cl>>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][N:11]2[C:10](=[O:17])[C:9]3[NH:18][C:19]([CH:20]([CH3:22])[CH3:21])=[N:7][C:8]=3[N:13]([CH2:14][CH3:15])[C:12]2=[O:16])=[CH:27][CH:26]=1Participants
Procedure
3.17 g (28.2 mM) of potassium t-butoxide (t-BuOK) were added to a solution of 6.11 g (27.5 mM) of 6-amino-1-ethyl-5-isobutyrylamino-uracil. At 0° C., 4.90 g (30.4 mM) of 4-chlorobenzylchloride were added. After 3 hr at 0-5° C., further 1.22 g t-BuOK and 2.45 g of 4-chloro-benzylchloride were added. After further 3 hr another 2.45 g of benzylchloride are supplemented. After 3 days (1 day is sufficient) the solution was neutralized with 1N HCl and the solvents evaporated. The residue was suspended in water, the solid collected and washed. The crude intermediate amide was heated under reflux in 100 ml of 1N NaOH and 10 ml of 1-propanol. After 1 hr the mixture was neutralized to pH 7 and extracted with chloroform. Crystallization from dichloromethane (mainly evaporated)--methanol gave 2.99 g (31.3%) of the title xanthine, mp 194-5° C. The mother liquors gave 6.33 g of impure material which was separated on 15 g of silica gel elutions with dichloromethane and gave additional 0.78 g (8.2%) of the xanthine.
Workup
- customthe solvents evaporated
- customthe solid collected
- washwashed
- temperatureThe crude intermediate amide was heated
- temperatureunder reflux in 100 ml of 1N NaOH
- waitAfter 1 hr the mixture was neutralized to pH 7
- extractionextracted with chloroform
- customCrystallization from dichloromethane (
- custommainly evaporated)--methanol
Sources & evidence
- ORD record
- ord-e7d367ec004c4ad2b9bcd828d6d260e6
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05977119
Reaction notes
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