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

HRID 1077476ノート

反応式

HRID 1077476 の反応式
[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

参加物

5

反応物 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

生成物 1

HCID 64489711H-Purine-2,6-dione, 3,7-dihydro-8-(2-(3,4-bis(methoxymethoxy)phenyl)ethenyl)-1,3-dipropyl-7-methyl-, (E)-収率 57%

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1987a820c4064bcb950922aadbfd1f3c
出典データセット
uspto-grants-1996_08
特許番号
US05543415

反応ノート

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