Water → 1H-Purine-2,6-dione, 3,7-dihydro-8-(2-(4-(4-aminobutoxy)phenyl)ethenyl )-1,3-diethyl-7-methyl-,(E)-

HRID 1077537Notes

Reaction equation

HRID 1077537 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:32]=[CH:31][C:12](/[CH:13]=[CH:14]/[C:15]2[N:23]([CH3:24])[C:22]3[C:21](=[O:25])[N:20]([CH2:26][CH3:27])[C:19](=[O:28])[N:18]([CH2:29][CH3:30])[C:17]=3[N:16]=2)=[CH:11][CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[OH-].[Na+]>O1CCCC1>[NH2:1][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:13]=[CH:14]/[C:15]2[N:23]([CH3:24])[C:22]3[C:21](=[O:25])[N:20]([CH2:26][CH3:27])[C:19](=[O:28])[N:18]([CH2:29][CH3:30])[C:17]=3[N:16]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 6448952155272-08-5

Product 1

HCID 64489531H-Purine-2,6-dione, 3,7-dihydro-8-(2-(4-(4-aminobutoxy)phenyl)ethenyl )-1,3-diethyl-7-methyl-,(E)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 187 (75 mg, 0.17 mmol) obtained in Reference Example 184 was dissolved in 7.5 ml of tetrahydrofuran. To the solution was added 90 mg (0.34 mmol) of triphenylphosphine, and the mixture was heated under reflux for 3 hours. Water (5 ml) was added thereto and the mixture was heated under reflux for further one hour. After cooling, a 2N aqueous solution of sodium hydroxide was added thereto, and the mixture was extracted with chloroform and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol/triethylamine) to give 74 mg (yield quant.) of Compound 188. The obtained crude crystals were further recrystallized from 2-propanol/water.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for further one hour
  5. temperatureAfter cooling
  6. extractionthe mixture was extracted with chloroform
  7. dry with materialdried over anhydrous sodium sulfate
  8. customfollowed by evaporation under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol/triethylamine)
  10. customto give

Sources & evidence

ORD record
ord-7c356a94f3694794aacba4b5d0cdc76b
Source dataset
uspto-grants-1996_08
Patent number
US05543415

Reaction notes

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