Potassium Carbonate → HCID 178509042, compound

HRID 2269042Notes

Reaction equation

HRID 2269042 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][CH2:28][CH:29]1[O:33][CH2:32][CH2:31][O:30]1>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:27][CH2:28][CH:29]2[O:33][CH2:32][CH2:31][O:30]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 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 1785090596-Amino-9-benzyl-8-hydroxy-2-mercaptopurine

Product 1

HCID 178509042HCID 178509042, compoundYield 60%

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-(2-bromoethyl)-1,3-dioxolane (0.14 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 (163 mg, yield 60%).

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-2d6c3d4a1cde49eebdaccc7d9b036ded
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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