Chloromethyl Methyl Ether → 1H-Purine-2,6-dione, 3,7-dihydro-8-(2-(3,4-bis(methoxymethoxy)phenyl)e thenyl)-1,3-dipropyl-7-methyl-, (E)-

HRID 1077476Notes

Reaction equation

HRID 1077476 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.C(N(C(C)C)CC)(C)C.Cl[CH2:39][O:40][CH3:41].[O:42]1[CH2:46]CC[CH2:43]1>>[CH3:39][O:40][CH2:41][O:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:28][CH2:43][O:42][CH3:46])/[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

5

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 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 64489711H-Purine-2,6-dione, 3,7-dihydro-8-(2-(3,4-bis(methoxymethoxy)phenyl)e thenyl)-1,3-dipropyl-7-methyl-, (E)-Yield 57%

Procedure

Compound 54 (300 mg, 0.78 mmol) obtained in Reference Example 51 was dissolved in 6 ml of tetrahydrofuran. To the solution were added 1.64 ml (9.41 mmol) of diisopropylethylamine and 1.64 ml (7.12 mmol) of chloromethylmethyl ether under ice-cooling in a stream of argon, and the mixture was heated under reflux for 3 hours. Ice was added to the reaction solution and the mixture was separated with chloroform-a saturated aqueous saline solution. The organic layer was dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) and recrystallized from hexane/ethyl acetate to give 211 mg (yield 57%) of Compound 68 as white needles.

Workup

  1. temperaturecooling in a stream of argon
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. additionIce was added to the reaction solution
  5. customthe mixture was separated with chloroform-a saturated aqueous saline solution
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customfollowed by evaporation under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)
  9. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-1987a820c4064bcb950922aadbfd1f3c
Source dataset
uspto-grants-1996_08
Patent number
US05543415

Reaction notes

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