Dimethylformamide → 6-Amino-9-benzyl-2-(2-methoxyethoxy)purine

HRID 2269168Notes

Reaction equation

HRID 2269168 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.[CH3:25][O:26][CH2:27][CH2:28][OH:29]>>[NH2:2][C:3]1[N:11]=[C:10]([O:29][CH2:28][CH2:27][O:26][CH3:25])[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 80192-MethoxyethanolHCID 2764829-Benzyl-2-chloro-9h-purin-6-amineHCID 5360545Sodium

Product 1

HCID 113355486-Amino-9-benzyl-2-(2-methoxyethoxy)purineYield 71%

Conditions

Temperature
130 °C

Procedure

Sodium (66 mg, 2.9 mmol) in 50 ml of 2-methoxyethanol was added 6-amino-9-benzyl-2-chloropurine (150 mg, 0.58 mmol) and DMF (10 ml). The mixture was heated at 130° C. for 6 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 concentrated in vacuo to dryness. The residue was purified with silica gel chromatography (3% methanol/chloroform) to give the subject compound (123 mg, yield 71%).

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. concentrationconcentrated in vacuo to dryness
  6. customThe residue was purified with silica gel chromatography (3% methanol/chloroform)

Sources & evidence

ORD record
ord-e460429b51b84a24ba450b314eb066f1
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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