Phenylmethyl 2-{3-[6-amino-2-(butyloxy)-8-(methyloxy)-9H-purin-9-yl]propyl}-1-piperidinecarboxylate → 2-(Butyloxy)-8-(methyloxy)-9-[3-(2-piperidinyl)propyl]-9H-purin-6-amine

HRID 2038164Notes

Reaction equation

HRID 2038164 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:35][CH3:36])[N:6]2[CH2:16][CH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]1C(OCC1C=CC=CC=1)=O>C(O)C.[Pd]>[CH2:12]([O:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[C:5]([O:35][CH3:36])[N:6]2[CH2:16][CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][NH:20]2)=[C:2]([NH2:1])[N:10]=1)[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 1

HCID 58306132Phenylmethyl 2-{3-[6-amino-2-(butyloxy)-8-(methyloxy)-9H-purin-9-yl]propyl}-1-piperidinecarboxylate2×

Product 1

HCID 583061842-(Butyloxy)-8-(methyloxy)-9-[3-(2-piperidinyl)propyl]-9H-purin-6-amineYield 77.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Phenylmethyl 2-{3-[6-amino-2-(butyloxy)-8-(methyloxy)-9H-purin-9-yl]propyl}-1-piperidinecarboxylate (for example, as prepared for Intermediate 11) (1.16 g, 2.336 mmol) in ethanol (130 mL) was hydrogenated over 10% palladium on carbon (0.497 g, 0.467 mmol) at ambient temperature overnight. The mixture was filtered through a Celite cartridge under nitrogen, washed with ethanol and evaporated in vacuo to give the title compound as a cream solid (0.66 g).

Workup

  1. filtrationThe mixture was filtered through a Celite cartridge under nitrogen
  2. washwashed with ethanol
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-40e9dd0af5854dbb8f5ba193b79c1a81
Source dataset
uspto-grants-2013_11
Patent number
US08575340B2

Reaction notes

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