Triethylamine → 9-(2-(2,2-Dimethyl-1,3-dioxan-5-yl)ethyl)-9H-purin-2-amine

HRID 2304772Notes

Reaction equation

HRID 2304772 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]=[C:13]2[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15][CH2:14]2)=[C:4](Cl)[N:3]=1.C(N(CC)CC)C>[Pd].C(OCC)(=O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]2[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15][CH2:14]2)=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 98614789H-Purin-2-amine, 6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-ylidene)ethyl]-

Product 1

HCID 109567979-(2-(2,2-Dimethyl-1,3-dioxan-5-yl)ethyl)-9H-purin-2-amineYield 74.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-[2-(2-amino-6-chloropurin-9-yl)]ethylidene-2,2-dimethyl-1,3-dioxane (0.45 g), 5% palladium on carbon (0.225 g) and triethylamine (0.22 ml) in ethyl acetate (22.5 ml) was hydrogenated at 50° C. for 18 hours at 50 p.s.i. The catalyst was removed by filtration and the filter washed with ethyl acetate. The combined filtrate and wash were concentrated under reduced pressure to give a gum which was purified by silica gel chromatography (eluted with dichloromethane/methanol 99:1 increasing to 97:3) to give the title compound (300 mg, 74% yield).

Workup

  1. customThe catalyst was removed by filtration
  2. washthe filter washed with ethyl acetate
  3. washThe combined filtrate and wash
  4. concentrationwere concentrated under reduced pressure
  5. customto give a gum which
  6. customwas purified by silica gel chromatography (eluted with dichloromethane/methanol 99:1 increasing to 97:3)

Sources & evidence

ORD record
ord-36b7a620518e45efa3bc7f1d426fdaf8
Source dataset
uspto-grants-2002_08
Patent number
US06437125B1

Reaction notes

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