Potassium Carbonate → 6-Amino-9-benzyl-2-(1,3-dioxolan-2-yl-methyl)thio-8-hydroxypurine

HRID 2269037Notes

Reaction equation

HRID 2269037 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([SH:11])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:19])[N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH:28]1[O:32][CH2:31][CH2:30][O:29]1>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:27][CH:28]2[O:32][CH2:31][CH2:30][O:29]2)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:19])[N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 780681,3-Dioxolane, 2-(bromomethyl)-HCID 1785090596-Amino-9-benzyl-8-hydroxy-2-mercaptopurine

Product 1

HCID 1785090406-Amino-9-benzyl-2-(1,3-dioxolan-2-yl-methyl)thio-8-hydroxypurineYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude 6-amino-9-benzyl-8-hydroxy-2-mercaptopurine (200 mg, 0.73 mmol) was suspended in dimethylformamide (80 ml). To the suspension were added potassium carbonate (150 mg, 1.1 mmol) and 2-bromomethyl-1,3-dioxolane (0.11 ml, 1.1 mmol) in order. The mixture was stirred at room temperature for 3 hours. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (3% methanol/chloroform) to give the subject compound (73 mg, yield 28%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography (3% methanol/chloroform)

Sources & evidence

ORD record
ord-ad111018143b4f718fbaf3a4aece670e
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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