1,3-Propanediol → 6-Amino-9-benzyl-2-(3-hydroxypropoxy)purine

HRID 2269160Notes

Reaction equation

HRID 2269160 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:24])[CH2:21][CH2:22][OH:23]>>[NH2:2][C:3]1[N:11]=[C:10]([O:23][CH2:22][CH2:21][CH2:20][OH:24])[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 104421,3-PropanediolHCID 2764829-Benzyl-2-chloro-9h-purin-6-amineHCID 5360545Sodium

Product 1

HCID 183327146-Amino-9-benzyl-2-(3-hydroxypropoxy)purineYield 51%

Conditions

Temperature
100 °C

Procedure

Sodium (80 mg, 3.5 mmol) in 3 ml of 1,3-propanediol was added 6-amino-9-benzyl-2-chloropurine (235 mg, 0.90 mmol). The mixture was heated at 100° C. for 3 hours. 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 (3% methanol/chloroform) to give the subject compound (137 mg, yield 51%).

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 (3% methanol/chloroform)

Sources & evidence

ORD record
ord-d3a7a6760f104f1db9aaba30639a3abd
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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