Adenine → HCID 54108631, compound

HRID 977508Notes

Reaction equation

HRID 977508 reaction equation
[H-].[Na+].[N:3]1[C:11]([NH2:12])=[C:10]2[C:6]([N:7]=[CH:8][NH:9]2)=[N:5][CH:4]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28]>CN(C)C=O>[NH2:12][C:11]1[N:3]=[CH:4][N:5]=[C:6]2[C:10]=1[N:9]=[CH:8][N:7]2[CH:14]=[CH:15][CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28]

Participants

5

Reactant 3

HCID 190AdenineHCID 24758Sodium hydrideHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 54108631HCID 54108631, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.4 g of sodium hydride were added to 9.6 g of adenine in 270 ml of dimethylformamide and the mixture was stirred for 2 hours and 30 minutes. 20 g of N-(4-bromobutyl)-phthalimide were added and the mixture was stirred at ambient temperature for 74 hours, followed by filtering. The solvent of the filtrate was evaporated and the precipitate was washed with ether, with water, with ethanol, then again with ether and dried. The residue was dissolved in methanol at 65° C. and chilled to obtain 15.00 g of the expected product.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 74 hours
  2. filtrationby filtering
  3. customThe solvent of the filtrate was evaporated
  4. washthe precipitate was washed with ether, with water, with ethanol
  5. dry with materialagain with ether and dried
  6. dissolutionThe residue was dissolved in methanol at 65° C.
  7. temperaturechilled

Sources & evidence

ORD record
ord-547f172e748044b0923664006daf9a1d
Source dataset
uspto-grants-1997_03
Patent number
US05614614

Reaction notes

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