9H-Purin-2-amine, 6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-ylidene)ethyl]- → 6-Chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-amine

HRID 2304773Notes

Reaction equation

HRID 2304773 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]=3[Cl:19])[CH2:4][O:3]1>[Pd].O1CCCC1>[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[CH2:4][O:3][C:2]([CH3:1])([CH3:21])[O:7][CH2:6]2)=[C:15]([Cl:19])[N:14]=1

Participants

4

Reactant 1

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

Product 1

HCID 117713466-Chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-amineYield 63.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

5% Palladium on carbon (1.5 g) in tetrahydrofuran (40 ml) was prehydrogenated for 30 min at 50 p.s.i. 2,2-Dimethyl-5-[2-(2-amino-6-chloropurin-9-yl)]ethylidene-1,3-dioxane (3.0 g) in tetrahydrofuran (80 ml) was added and washed in with tetrahydrofuran (30 ml). The mixture was hydrogenated overnight at 50 p.s.i. with stirring. The catalyst was removed by filtration to give a colourless solution. The solvent was removed under reduced pressure and the residue recrystallised from IPA to give the title compound (1.92 g, 62.2% yield).

Workup

  1. washwashed in with tetrahydrofuran (30 ml)
  2. customThe catalyst was removed by filtration
  3. customto give a colourless solution
  4. customThe solvent was removed under reduced pressure
  5. customthe residue recrystallised from IPA

Sources & evidence

ORD record
ord-0e8ce6ee75cc441b836200de2f8d10a4
Source dataset
uspto-grants-2002_08
Patent number
US06437125B1

Reaction notes

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