2-Methoxyethylamine → 6-Amino-9-benzyl-2-(2-methoxyethyl)aminopurine

HRID 2269142Notes

Reaction equation

HRID 2269142 reaction equation
[NH2:1][C:2]1[N:10]=[C:9](Cl)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:19][O:20][CH2:21][CH2:22][NH2:23]>C(O)CCC>[NH2:1][C:2]1[N:10]=[C:9]([NH:23][CH2:22][CH2:21][O:20][CH3:19])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 183327796-Amino-9-benzyl-2-(2-methoxyethyl)aminopurineYield 72%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

6-Amino-9-benzyl-2-chloropurine (10 mg, 0.385 mmol) and 2-methoxyethylamine in 2 ml of butanol were heated at 120° C. for 9 hours in autoclave. The reaction mixture was concentrated in vacuo to dryness and to the residue was added water. The mixture was extracted with chloroform and 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 (83 mg, yield 72%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to dryness and to the residue
  2. additionwas 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-cb4af91468d440c98be69de344379904
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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