Ethylene Glycol → HCID 15509335, compound

HRID 2269157Notes

Reaction equation

HRID 2269157 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.[CH2:20]([OH:23])[CH2:21][OH:22]>>[NH2:2][C:3]1[N:11]=[C:10]([O:22][CH2:21][CH2:20][OH:23])[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

4

Reactant 3

HCID 174Ethylene GlycolHCID 2764829-Benzyl-2-chloro-9h-purin-6-amineHCID 5360545Sodium

Product 1

HCID 15509335HCID 15509335, compoundYield 70%

Conditions

Temperature
100 °C

Procedure

To sodium (74 mg, 3.2 mmol) in 5 ml of ethylene glycol were added 6-amino-9-benzyl-2-chloropurine (157 mg, 0.58 mmol). The mixture was heated at 100° C. for 4 hours and concentrated in vacuo to dryness. To the residue was added water and the mixture was extracted with chloroform. The organic layer was dried on magnesium sulfate and the solvent was removed in vacuo. The residue was purified with silica gel chromatography (3% methanol/chloroform) to give the subject compound (121 mg, yield 70%).

Workup

  1. concentrationconcentrated 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 magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified with silica gel chromatography (3% methanol/chloroform)

Sources & evidence

ORD record
ord-89497b78a51c481389f84eef7a50f540
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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