Dimethylformamide → 6-Amino-9-benzyl-2-(3-ethoxypropoxy)purine

HRID 2269163Notes

Reaction equation

HRID 2269163 reaction equation
[Na].[NH2:2][C:3]1[N:11]=[C:10](Cl)[N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN(C=O)C.[CH2:25]([O:27][CH2:28][CH2:29][CH2:30][OH:31])[CH3:26]>>[NH2:2][C:3]1[N:11]=[C:10]([O:31][CH2:30][CH2:29][CH2:28][O:27][CH2:25][CH3:26])[N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81093-Ethoxy-1-propanolHCID 2764829-Benzyl-2-chloro-9h-purin-6-amineHCID 5360545Sodium

Product 1

HCID 183327566-Amino-9-benzyl-2-(3-ethoxypropoxy)purineYield 76%

Conditions

Temperature
120 °C

Procedure

To sodium (150 mg, 6.5 mmol) in 5 ml of 3-ethoxypropanol were added 6-amino-9-benzyl-2-chloropurine (500 mg, 1.93 mmol) and DMF (10 ml). The mixture was heated at 120° C. for 1 hour. The reaction mixture was concentrated in vacuo to dryness. To the residue was added water and the mixture was extracted with chloroform. The organic layer was dried on sodium sulfate and the solvent was removed. The residue was purified with silica gel chromatography (2% methanol/chloroform) to give the subject compound (481 mg, yield 76%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to dryness
  2. additionTo the residue was added water
  3. extractionthe mixture was extracted with chloroform
  4. customThe organic layer was dried on sodium sulfate
  5. customthe solvent was removed
  6. customThe residue was purified with silica gel chromatography (2% methanol/chloroform)

Sources & evidence

ORD record
ord-ddad9cc2741f4232b1b56293721a59f3
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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