Phenylmethyl 4-{4-[6-amino-2-(butylamino)-8-(methyloxy)-9H-purin-9-yl]butyl}-1-piperidinecarboxylate → N2-Butyl-8-(methyloxy)-9-[4-(4-piperidinyl)butyl]-9H-purine-2,6-diamine

HRID 2403864Notes

Reaction equation

HRID 2403864 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:36][CH3:37])[N:6]2[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23](C(OCC2C=CC=CC=2)=O)[CH2:22][CH2:21]1>[Pd].C(O)C>[CH2:12]([NH:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[C:5]([O:36][CH3:37])[N:6]2[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]2[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]2)=[C:2]([NH2:1])[N:10]=1)[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 1

HCID 58306197Phenylmethyl 4-{4-[6-amino-2-(butylamino)-8-(methyloxy)-9H-purin-9-yl]butyl}-1-piperidinecarboxylate

Product 1

HCID 58306194N2-Butyl-8-(methyloxy)-9-[4-(4-piperidinyl)butyl]-9H-purine-2,6-diamineYield 57.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of phenylmethyl 4-{4-[6-amino-2-(butylamino)-8-(methyloxy)-9H-purin-9-yl]butyl}-1-piperidinecarboxylate ammoniate (372 mg, 0.730 mmol) and 10% palladium on carbon (155 mg, 0.146 mmol) in ethanol (5 ml) was hydrogenated at atmospheric pressure and room temperature for 18 hours. The catalyst was filtered through Celite and the filtrate concentrated in vacuo. The residue was dissolved in 1:1 MeOH:DMSO (3 ml) and purified by Mass Directed AutoPrep (Method A). The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the title compound as a white gum (157 mg).

Workup

  1. filtrationThe catalyst was filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in 1:1 MeOH
  4. customDMSO (3 ml) and purified by Mass Directed AutoPrep (Method A)
  5. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record
ord-d2acfa85e3354a75aab9d606f2873448
Source dataset
uspto-grants-2014_08
Patent number
US08802684B2

Reaction notes

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