Water → 151539-57-0

HRID 375338Notes

Reaction equation

HRID 375338 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[OH:28])/[CH:5]=[CH:6]/[C:7]1[N:15]([CH3:16])[C:14]2[C:13](=[O:17])[N:12]([CH2:18][CH2:19][CH3:20])[C:11](=[O:21])[N:10]([CH2:22][CH2:23][CH3:24])[C:9]=2[N:8]=1.CI.[C:31](=O)([O-])[O-].[Li+].[Li+].O>CN(C)C=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:28][CH3:31])/[CH:5]=[CH:6]/[C:7]1[N:15]([CH3:16])[C:14]2[C:13](=[O:17])[N:12]([CH2:18][CH2:19][CH3:20])[C:11](=[O:21])[N:10]([CH2:22][CH2:23][CH3:24])[C:9]=2[N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11125Lithium Carbonate2×HCID 135665338(8E)-8-[(2Z)-2-(3-hydroxy-4-oxo-1-cyclohexa-2,5-dienylidene)ethylidene ]-7-methyl-1,3-dipropyl-9H-purine-2,6-dione

Product 1

HCID 6448807151539-57-0Yield 31.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Compound 53 (500 mg, 1.30 mmol) obtained in Reference Example 46 was dissolved in 10 ml of dimethylformamide. To the solution were added 0.40 ml (6.43 mmol) of methyl iodide and 400 mg (6.50 mmol) of lithium carbonate, and the mixture was stirred at 80° C. for 5 hours. Water was added thereto to dissolve lithium carbonate and 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 purified by silica gel column chromatography (eluent: chloroform) to give 162 mg (yield 31%) of Compound 63 as yellow grains.

Workup

  1. filtrationwere 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 purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-a639d86dac454260b05bf37dbdab3301
Source dataset
uspto-grants-1996_01
Patent number
US05484920

Reaction notes

Loading…