Hydrochloric Acid → HCID 15886850, compound

HRID 377184Notes

Reaction equation

HRID 377184 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]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 21715769HCID 21715769, compoundHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 15886850HCID 15886850, compoundYield 56.7%

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-chlorobenzylclhloride were added. After 3 hours at 0-5° C., further 1.22 g t-BuOK and 2.45 g of 4-chloro-benzylchloride were added. After further 3 hours another 2.45 g of benzylchloride are supplemented. After 3 days, 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 hour, 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

  1. additionAt 0° C., 4.90 g (30.4 mM) of 4-chlorobenzylclhloride were added
  2. waitAfter 3 days
  3. customthe solvents evaporated
  4. customthe solid collected
  5. washwashed
  6. temperatureThe crude intermediate amide was heated
  7. temperatureunder reflux in 100 ml of 1N NaOH
  8. waitAfter 1 hour
  9. extractionextracted with chloroform
  10. customCrystallization from dichloromethane (
  11. custommainly evaporated)--methanol

Sources & evidence

ORD record
ord-0e31f689ee4541f28f1f8aad7ba92779
Source dataset
uspto-grants-2000_02
Patent number
US06025361

Reaction notes

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