Water → 151539-47-8

HRID 375334Notes

Reaction equation

HRID 375334 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1O)/[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.[CH2:29](I)[CH3:30].[C:32](=[O:35])([O-])[O-].[K+].[K+].O.[CH3:39]N(C)C=O>>[CH2:29]([O:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:35][CH2:32][CH3:39])/[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)[CH3:30]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium 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 6448800151539-47-8Yield 53%

Procedure

Compound 53 (390 mg, 1.01 mmol) obtained in Reference Example 46 was dissolved in 10 ml of dimethylformamide. To the solution were added 0.20 ml (2.50 mmol) of ethyl iodide and 420 mg (3.04 mmol) of potassium carbonate, and the mixture was stirred overnight at room temperature. Water was added thereto to dissolve potassium carbonate and deposited crystals were collected by filtration. The collected crude crystals were recrystallized from hexane/ethyl acetate to give 237 mg (yield 53%) of Compound 54 as pale yellow needles.

Workup

  1. filtrationwere collected by filtration
  2. customThe collected crude crystals
  3. customwere recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-6dca24f20e024f28b3f3a0eb83fc92d7
Source dataset
uspto-grants-1996_01
Patent number
US05484920

Reaction notes

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