1,1'-Carbonyldiimidazole → 9-[1,3-Bis(imidazol-1-ylcarbonyloxy)-2-propoxymethyl]-guanine

HRID 1194804Notes

Reaction equation

HRID 1194804 reaction equation
[OH2:1].[OH:2][CH2:3][CH:4]([O:7][CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:14](=[O:18])[NH:13][C:12]([NH2:19])=[N:11][C:10]1=2)[CH2:5][OH:6].[C:20]([N:27]1[CH:31]=[CH:30][N:29]=[CH:28]1)(N1C=CN=C1)=[O:21]>CN(C)C=O>[N:9]1([C:8]([O:2][CH2:3][CH:4]([O:7][CH2:8][N:9]2[CH:17]=[N:16][C:15]3[C:14](=[O:18])[NH:13][C:12]([NH2:19])=[N:11][C:10]2=3)[CH2:5][O:6][C:20]([N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)=[O:21])=[O:1])[CH:10]=[CH:15][N:16]=[CH:17]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 1360789939-[[2-Hydroxy-1-(hydroxymethyl)ethoxy]methyl]guanine hydrate

Product 1

HCID 1363368949-[1,3-Bis(imidazol-1-ylcarbonyloxy)-2-propoxymethyl]-guanineYield 83.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 55 mg (0.2 mmole) of 9-(1,3-dihydroxy-2-propoxymethyl)guanine monohydrate, 130 mg (0.8 mmole) of 1,1'-carbonyldiimidazole, and 2 ml of dry dimethylformamide was stirred under nitrogen at 95°-100° for 1.5 hours, during which time a clear solution was obtained followed by precipitation of product. After cooling, the precipitate was collected on a filter and washed with some dimethylformamide and then with acetone to give 37 mg of white crystals, m.p. 252°-253° dec. The NMR spectrum was in accord with the assigned structure.

Workup

  1. customwas obtained
  2. customfollowed by precipitation of product
  3. temperatureAfter cooling
  4. customthe precipitate was collected on
  5. filtrationa filter
  6. washwashed with some dimethylformamide

Sources & evidence

ORD record
ord-067673a5e91f4a86be7856f74ff5b577
Source dataset
uspto-grants-1989_03
Patent number
US04816447

Reaction notes

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