Potassium Carbonate → HCID 58306160, compound

HRID 2403882Notes

Reaction equation

HRID 2403882 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[NH:6][C:7]([NH2:16])=[C:8]2[C:12]([N:13]=1)=[N:11][C:10]([O:14][CH3:15])=[N:9]2)[CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][CH2:27][CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1>CN(C=O)C.ClCCl>[NH2:16][C:7]1[N:6]=[C:5]([O:4][CH:2]([CH3:1])[CH3:3])[N:13]=[C:12]2[C:8]=1[N:9]=[C:10]([O:14][CH3:15])[N:11]2[CH2:24][CH2:25][CH2:26][CH2:27][CH:28]1[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[CH2:32][CH2:33]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10358619tert-Butyl 4-(4-bromobutyl)piperidine-1-carboxylateHCID 178494010HCID 178494010, compound

Product 1

HCID 58306160HCID 58306160, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(1-methylethyl)oxy]-8-(methyloxy)-1H-purin-6-amine (37 mg, 0.166 mmol) in DMF (0.5 ml) was added potassium carbonate (55 mg, 0.398 mmol) followed by a solution of 1,1-dimethylethyl 4-(4-bromobutyl)-1-piperidinecarboxylate (58 mg, 0.181 mmol) in DMF (0.2 ml) and the mixture was stirred at room temperature for 72 hours. The mixture was diluted with dichloromethane (5 ml) and washed with water (5 ml). The layers were separated using a hydrophobic frit, the aqueous layer was extracted again with dichloromethane (5 ml) and the combined organic extracts were evaporated. The residue was dissolved in methanol (0.6 ml) and purified by MDAP (Method A). The appropriate fractions were combined and evaporated under a stream of nitrogen in a blowdown apparatus to give the title compound as a colourless gum (32 mg).

Workup

  1. washwashed with water (5 ml)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted again with dichloromethane (5 ml)
  4. customthe combined organic extracts were evaporated
  5. dissolutionThe residue was dissolved in methanol (0.6 ml)
  6. custompurified by MDAP (Method A)
  7. customevaporated under a stream of nitrogen in a blowdown apparatus

Sources & evidence

ORD record
ord-7fe25246a6214290a7ab42902a2f03c7
Source dataset
uspto-grants-2014_08
Patent number
US08802684B2

Reaction notes

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