Adenine → 9-(Phenylmethyl)-9H-purin-6-amine

HRID 1594604Notes

Reaction equation

HRID 1594604 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:13]([N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 190AdenineHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 202629-(Phenylmethyl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Adenine (1 mmol) in DMF was treated with sodium hydride (1.2 mmol) followed by benzyl bromide (1.2 mmol) at room temperature under nitrogen. The resulting mixture was warmed at 100° C. for 2 h. The cooled reaction mixture was evaporated to dryness. Extraction and chromatography afforded N9-benzyladenine.

Workup

  1. customThe cooled reaction mixture
  2. customwas evaporated to dryness
  3. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-0200b462343b426596d1c64fd004cbca
Source dataset
uspto-grants-2001_09
Patent number
US06284748B1

Reaction notes

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