Adenine → HCID 14257974, compound

HRID 1459174Notes

Reaction equation

HRID 1459174 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.C([O:15][P:16]([CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26]Br)([O:18]CC)=[O:17])C>CN(C=O)C>[P:16]([CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][N:7]1[CH:8]=[N:9][C:10]2[C:6]1=[N:5][CH:4]=[N:3][C:11]=2[NH2:12])([OH:18])([OH:17])=[O:15]

Participants

5

Reactant 3

HCID 190AdenineHCID 24758Sodium hydrideHCID 54403749HCID 54403749, compound

Product 1

HCID 14257974HCID 14257974, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of 0.962 g (22.8 mmol) of 57% NaH in 150 ml of distilled DMF was added in one portion 3.363 gm (24.9 mmol) of adenine. The mixture was heated at 80° for 1 hr. and then cooled to 300 and 6.30 g (20.7 mmol) of 4-(diethylphosphonomethoxy)-1-bromobutane was added and the mixture was warmed to 60° and stirred for 2 hrs. The solvent was then removed under high vacuum and the residue was triturated three times with 100 ml of CH2Cl2 and filtered. The combined filtrates were evaporated and purified by SiO2 chromatography to give 4.9 g (66%) of Ia product as a white crystalline material mp 67°.

Workup

  1. temperatureThe mixture was heated at 80° for 1 hr
  2. additionwas added
  3. temperaturethe mixture was warmed to 60°
  4. customThe solvent was then removed under high vacuum
  5. customthe residue was triturated three times with 100 ml of CH2Cl2
  6. filtrationfiltered
  7. customThe combined filtrates were evaporated
  8. custompurified by SiO2 chromatography

Sources & evidence

ORD record
ord-44a40e0e856d423bb8dbb1d6c5f06e24
Source dataset
uspto-grants-1998_12
Patent number
US05854228

Reaction notes

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