Methanol → 6-chloro-9-[(1RS,4SR)-4-hydroxy-cyclopent-2-en-1-yl]purine

HRID 1780758Notes

Reaction equation

HRID 1780758 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[O:11]1[C:13]2[CH2:14][CH2:15][CH2:16][C:12]1=2.CO>[Pd].O1CCCC1>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:15]1[CH2:16][CH:12]([OH:11])[CH:13]=[CH:14]1

Participants

6

Reactant 3

HCID 887MethanolHCID 53592776-ChloropurineHCID 22121731HCID 22121731, compound

Product 1

HCID 109990106-chloro-9-[(1RS,4SR)-4-hydroxy-cyclopent-2-en-1-yl]purineYield 25%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Trimethylsilylated 6-chloropurine (prepared from 50 g (0.32 mol) of 6-chloropurine) is stirred with 5 mol % of the palladium(0) catalyst described above and an equivalent amount of epoxycyclopentene in tetrahydrofuran at room temperature for 24 hours. The reaction solution is heated with methanol for 1.5 hours, the precipitate formed is filtered off with suction, the resulting solution is concentrated and the residue is chromatographed over silica gel using methylene chloride/methanol 20/1. 18.9 g (25% of theory) of 6-chloro-9-[(1RS,4SR)-4-hydroxy-cyclopent-2-en-1-yl]purine (Example 1.5.1.) are obtained as yellowish crystals of melting point 118° C. 1H-NMR (270 MHz, d6 -DMSO), δ[ppm]: 8.80 (s, 1H), 8.62 (s, 1H), 6.25 (m, 1H), 6.08 (m, 1H), 5.60 (m, 1H), 5.31 (d, 1H), 4.76 (m, 1H), 2.95 (m, 1H), 1.81 (m, 1H).

Workup

  1. customat room temperature
  2. customfor 24 hours
  3. customthe precipitate formed
  4. filtrationis filtered off with suction
  5. concentrationthe resulting solution is concentrated
  6. customthe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-6a735af9520a4fa2abe06db3c83e26ae
Source dataset
uspto-grants-1997_05
Patent number
US05631259

Reaction notes

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