Water → Acetic acid, (4-(2-(1,3-diethyl-2,3,6,7-tetrahydro-7-methyl-2,6-dioxo- 1H-purin-8-yl)ethenyl)phenoxy)-, ethyl ester, (E)-

HRID 375374Notes

Reaction equation

HRID 375374 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+].Cl[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].O>CN(C)C=O>[CH2:37]([O:36][C:34]([CH2:33][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)=[O:35])[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 7751Ethyl chloroacetateHCID 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 6448954Acetic acid, (4-(2-(1,3-diethyl-2,3,6,7-tetrahydro-7-methyl-2,6-dioxo- 1H-purin-8-yl)ethenyl)phenoxy)-, ethyl ester, (E)-Yield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 175 (300 mg, 0.88 mmol) obtained in Reference Example 114 was dissolved in 10 ml of dimethylformamide. To the solution were added 731 mg (5.29 mmol) of potassium carbonate and 0.47 ml (4.41 mmol) of ethyl chloroacetate, and the mixture was stirred at room temperature for 2 hours. Water was added thereto 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 341 mg (yield 91%) of Compound 180 as pale 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-2a1aee767db54290b2172071cad6cd9d
Source dataset
uspto-grants-1996_01
Patent number
US05484920

Reaction notes

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