9-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-3H-purin-6-one → HCID 178520964, compound

HRID 2209758Notes

Reaction equation

HRID 2209758 reaction equation
[C@@H:1]1([N:8]2[C:17]3[N:16]=[CH:15][N:14]=[C:12]([OH:13])[C:11]=3[N:10]=[CH:9]2)[O:7][C@H:4]([CH2:5][OH:6])[CH:3]=[CH:2]1>C(O)C.O.[Pd]>[C@@H:1]1([N:8]2[C:17]3[N:16]=[CH:15][N:14]=[C:12]([OH:13])[C:11]=3[N:10]=[CH:9]2)[O:7][C@H:4]([CH2:5][OH:6])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 1785209639-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-3H-purin-6-one

Product 1

HCID 178520964HCID 178520964, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19096565Water ethanolSolvent

Procedure

A solution of the olefin 8 (0.38 g, 1.6 mmol) in a mixture of ethanol-water (4:1) (70 ml) was hydrogenated in the presence of 10% Pd/C (0.07 g) at 50 psi for 6 h. The mixture was filtered through celite, the filtrate was concentrated, and cooled. The solid obtained was filtered and dried to yield 0.3 g (78%) of 11: mp softens at 184°-186° C., but does not melt up to 300° C.; 1H NMR (DMSO-d6) δ 1.72-2.48 (4H, m, 2' and 3'-H), 3.21-3.67 (2H, m, 5'-H), 4.17-4.38 (1H, m, 4'-H), 4.72 (1 H br s, OH, exchangeable), 6.20 (1H, dd, J=3.81 Hz, 4.1 Hz, 1'-H), 7.90 (1H, s, 8-H), 8.15 (1H, s, 2-H), 12.20 (1 H, br s, NH).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. temperaturecooled
  4. customThe solid obtained
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-76d87c62b919418999dc5ab27c79d52d
Source dataset
uspto-grants-1995_10
Patent number
US05455339

Reaction notes

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