Ethylenediamine → 2,6-Diaminopurine

HRID 1862011Notes

Reaction equation

HRID 1862011 reaction equation
[C@@H]1([N:9]2[C:19]3[N:18]=[C:16]([NH2:17])[NH:15][C:13](=O)[C:12]=3[N:11]=[CH:10]2)O[C@H](CO)[C@@H](O)C1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N)C[NH2:35]>N1C=CC=CC=1>[NH2:17][C:16]1[N:18]=[C:19]2[C:12]([NH:11][CH:10]=[N:9]2)=[C:13]([NH2:35])[N:15]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 9845Trifluoroacetic anhydrideHCID 135398592Deoxyguanosine

Product 1

HCID 309762,6-Diaminopurine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To 2′-deoxyguanosine (2 mmol), dried by coevaporation with pyridine, suspended in 40 mL of pyridine and cooled in an ice bath under an argon atmosphere, trifluoroacetic anhydride (16 mmol) is added following the procedure of Kung and Jones (Tetraheron Lett., 32, 3919, 1991). After 40 minutes, ethylenediamine (30 mmol) is added and stirred for 24 h at room temperature. The reaction mixture is concentrated and purified by silica column chromatography. The product is guanylated with reagent 5 as in Example 8 and protected at N2-position with an isobutyryl group by treating with isobutyric anhydride, 5′-dimethoxytritylated at the 5′-position and purified. The resulting compound is treated with benzoic anhydride (N6 protection) and then phosphitylated following the procedures described above to afford the 2,6-diaminopurine derivative functionalized at the 6-position (35).

Workup

  1. temperaturecooled in an ice bath under an argon atmosphere
  2. concentrationThe reaction mixture is concentrated
  3. custompurified by silica column chromatography
  4. additionby treating with isobutyric anhydride, 5′-dimethoxytritylated at the 5′-position and
  5. custompurified
  6. additionThe resulting compound is treated with benzoic anhydride (N6 protection)

Sources & evidence

ORD record
ord-38d4fbce7db347f7a6f61bef9c4b1f52
Source dataset
uspto-grants-2003_03
Patent number
US06534639B1

Reaction notes

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