HCID 86612905, compound → HCID 178434909, compound

HRID 915878Notes

Reaction equation

HRID 915878 reaction equation
[CH3:1][C@@:2]1([OH:24])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:23]=[C:14]2[CH:15]=[CH:16][C:17]3[C:18](=[O:22])[NH:19][N:20]=[CH:21][C:12]([C:13]=32)=[N:11]1>CO.[Pd]>[CH3:1][C@@:2]1([OH:24])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:23]=[C:14]2[CH2:15][CH2:16][C:17]3[C:18](=[O:22])[NH:19][N:20]=[CH:21][C:12]([C:13]=32)=[N:11]1

Participants

4

Reactant 1

HCID 86612905HCID 86612905, compound

Product 1

HCID 178434909HCID 178434909, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tricyclic nucleoside 6.6 (20 mg, 0.06 mmol) and 10% Pd/C (12.8 mg, 0.2 eq.) in 20 mL of MeOH under H2 pressure (32 psi) was shaken for 7 hr at room temperature. The mixture was filtered through 0.45 μM filter. The combined filtrates were evaporated and purified on a silica gel column with 5% MeOH in CH2Cl2. 12 mg of pure compound 8.1 was obtained (yield 60%). 1H NMR (300 MHz, DMSO-d6): δ 10.65 (br s, 1H, NH), 8.37 (s, 1H, H-4), 7.48 (s, 1H, H-1), 6.12 (s, 1H, H-1′), 5.05 (m, 3H, 3×OH), 3.89-3.12 (m, 4H, H-3′, H-4′, 2×H-5′), 2.86-2.74 (m, 4H, 2×H-8, 2×H-9), 0.64 (s, 3H, CH3); LCMS: ES-MS 393.6 (M+CH3COO).

Workup

  1. filtrationThe mixture was filtered through 0.45 μM
  2. filtrationfilter
  3. customThe combined filtrates were evaporated
  4. custompurified on a silica gel column with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-3b007f4e60f94fef99dfc68f53777f92
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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