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Potassium Carbonate → HCID 58306160, compound

HRID 1044945
Notes
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Reaction equation

HRID 1044945 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent

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-282046417d3d473884a9c69f4dcf45a9
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08563717B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes