Water → 155272-06-3

HRID 1081846Notes

Reaction equation

HRID 1081846 reaction equation
[CH2:1]([N:3]1[C:12](=[O:13])[C:11]2[N:10]([CH3:14])[C:9](/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[N:8][C:7]=2[N:6]([CH2:24][CH3:25])[C:4]1=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.O>CN(C)C=O>[CH2:32]([O:23][C:20]1[CH:19]=[CH:18][C:17](/[CH:16]=[CH:15]/[C:9]2[N:10]([CH3:14])[C:11]3[C:12](=[O:13])[N:3]([CH2:1][CH3:2])[C:4](=[O:5])[N:6]([CH2:24][CH3:25])[C:7]=3[N:8]=2)=[CH:22][CH:21]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium Carbonate2×HCID 1356653431H-Purine-2,6-dione, 3,7-dihydro-1,3-diethyl-8-(2-(4-hydroxyphenyl)eth enyl)-7-methyl-, (E)-

Product 1

HCID 6448950155272-06-3Yield 53.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Compound 175 (100 mg, 0.29 mmol) obtained in Reference Example 114 was dissolved in 2 ml of dimethylformamide. To the solution were added 162 mg (1.17 mmol) of potassium carbonate and 0.28 ml (2.35 mmol) of benzyl bromide, and the mixture was stirred at 80° C. for 2.5 hours. Water was added thereto under ice cooling to dissolve potassium carbonate and the deposited crystals were collected by filtration. The collected crude crystals were dissolved in chloroform, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was recrystallized from hexane/ethyl acetate to give 67 mg (yield 53%) of Compound 176 as yellow needles.

Workup

  1. filtrationthe deposited crystals were collected by filtration
  2. customThe collected crude crystals
  3. dissolutionwere dissolved in chloroform
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customfollowed by evaporation under reduced pressure
  7. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-17065513cb074ce9ae3c1b8961a7ea2f
Source dataset
uspto-grants-1996_12
Patent number
US05587378

Reaction notes

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