Potassium Carbonate → 9-(1-tert-Butoxycarbonylpiperidin-4-ylethyl)-8-methoxy-2-(2-methoxyethoxy)adenine

HRID 1666201Notes

Reaction equation

HRID 1666201 reaction equation
[CH3:1][O:2][C:3]1[NH:11][C:10]2[C:5](=[N:6][C:7]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[N:8][C:9]=2[NH2:12])[N:4]=1.C(=O)([O-])[O-].[K+].[K+].[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([CH2:37][CH2:38]OS(C)(=O)=O)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>CN(C=O)C>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([CH2:37][CH2:38][N:4]2[C:3]([O:2][CH3:1])=[N:11][C:10]3[C:5]2=[N:6][C:7]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[N:8][C:9]=3[NH2:12])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15229596tert-Butyl 4-(2-((methanesulfonyl)oxy)ethyl)piperidine-1-carboxylateHCID 576997918-Methoxy-2-(2-methoxyethoxy)-9H-purine-6-amine

Product 1

HCID 592880219-(1-tert-Butoxycarbonylpiperidin-4-ylethyl)-8-methoxy-2-(2-methoxyethoxy)adenineYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

8-Methoxy-2-(2-methoxyethoxy)adenine (3.27 g, 13.7 mmol) was dissolved in DMF (75 ml), and thereto were added potassium carbonate (1.89 g, 13.7 mmol) and 4-[2-(methanesulfonyloxy)ethyl]piperidine-1-carboxylic acid tert-butyl ester (4.21 g, 13.7 mmol), and the mixture was stirred at 60° C. for 2.5 hours. The mixture was cooled to room temperature, and the carbonate salt was removed by filtration, and the filtrate was concentrated. To the residue was added water, and the mixture was extracted three times with chloroform. The resultant was dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column (chloroform/methanol=200/1 to 100/1) to give the subtitle compound (3.62 g, 8.04 mmol) as a white solid. Yield: 60%.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe carbonate salt was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. additionTo the residue was added water
  5. extractionthe mixture was extracted three times with chloroform
  6. dry with materialThe resultant was dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column (chloroform/methanol=200/1 to 100/1)

Sources & evidence

ORD record
ord-49af5b3e7cbe4db5a206163a0bd009bd
Source dataset
uspto-grants-2011_10
Patent number
US08044056B2

Reaction notes

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