2-Methoxyethanol → HCID 18332788, compound

HRID 2269147Notes

Reaction equation

HRID 2269147 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1.[CH3:19][O:20][CH2:21][CH2:22][OH:23]>[Na]>[NH2:1][C:2]1[N:10]=[C:9]([O:23][CH2:22][CH2:21][O:20][CH3:19])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 80192-MethoxyethanolHCID 114364636-Amino-9-(4-fluorobenzyl)purine

Product 1

HCID 18332788HCID 18332788, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 5360545SodiumSolvent

Conditions

Temperature
20 °C

Procedure

6-Amino-9-(4-fluorobenzyl)purine (100 mg, 0.36 mmol) was dissolved in 30 ml of sodium 2-mehoxyethoxide in 2-methoxyethanol and the solution was heated at 20° C. for 3 hours. 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 washed with water, dried on sodium sulfate and concentrated in vacuo to dryness. The residue was purified with silica gel chromatography (2% methanol/chloroform) to give the subject compound (109 mg, yield 95%).

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. washthe organic layer was washed with water
  5. customdried on sodium sulfate
  6. concentrationconcentrated in vacuo to dryness
  7. customThe residue was purified with silica gel chromatography (2% methanol/chloroform)

Sources & evidence

ORD record
ord-362e64275a76417da4b34e10cad399eb
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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