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

HRID 393383Notes

Reaction equation

HRID 393383 reaction equation
[CH3:1][C:2]1([CH3:21])[O:7][CH2:6][C:5](=[CH:8][CH2:9][N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][C:13]([NH2:20])=[N:14][C:15]=3Cl)[CH2:4][O:3]1.C(N(CC)CC)C>[Pd].C(OCC)(=O)C>[NH2:20][C:13]1[N:12]=[C:11]2[C:16]([N:17]=[CH:18][N:10]2[CH2:9][CH2:8][CH:5]2[CH2:6][O:7][C:2]([CH3:21])([CH3:1])[O:3][CH2:4]2)=[CH:15][N:14]=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 2,2-dimethyl-5-[2-(2-amino-6-chloropurin-9-yl)]ethylidene-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-1b5e664ae96a49129e1e48b3cd19990a
Source dataset
uspto-grants-2004_10
Patent number
US06806375B2

Reaction notes

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