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 393384Notes

Reaction equation

HRID 393384 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 hydrogentated 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-e7e02d2fd8214f6ca8647d6838c171d5
Source dataset
uspto-grants-2004_10
Patent number
US06806375B2

Reaction notes

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