Sodium Acetate → 5-Acetylamino-3-(2,3,5'-tri-O-acetyl-beta-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-one

HRID 549798Notes

Reaction equation

HRID 549798 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7](Cl)[C:8]2[S:13][C:12](=[O:14])[N:11]([C@@H:15]3[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:16]3[O:17][C:18](=[O:20])[CH3:19])[C:9]=2[N:10]=1)(=[O:3])[CH3:2].C([O-])(=O)C.[Na+]>[Pd].C(O)C>[C:1]([NH:4][C:5]1[N:6]=[CH:7][C:8]2[S:13][C:12](=[O:14])[N:11]([C@@H:15]3[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:16]3[O:17][C:18](=[O:20])[CH3:19])[C:9]=2[N:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 865973555-Acetylamino-7-chloro-3-(2,3,5'-tri-O-acetyl-beta-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-one

Product 1

HCID 685634785-Acetylamino-3-(2,3,5'-tri-O-acetyl-beta-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-oneYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (862 mg) was added to a solution of 81 (2.07 mg, 4.12 mmol), sodium acetate (675 mg, 8.23 mmol) and absolute ethanol (100 mL) under nitrogen. The mixture was stirred under 250-300 psi H2 (g) in a bomb for a period of 48 h. The mixture was filtered through Celite®, washed with ethyl acetate (200 mL), and concentrated to a yellow solid. The mixture was diluted with H2O (200 mL) and extracted with CH2Cl2 (3×100 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated. The residue was purified via Flash chromatography (SiO2, 10% Acetone-CHCl3) to afford 82 (1.74 g, 90%) as a white powder: 1H NMR (400 MHz, d6-DMSO) δ 10.78 (s, 1H), 8.82 (s, 1H), 6.10 (d, J=4.0 Hz, 1H), 6.04 (dd, J=6.0, 4.0 Hz, 1H), 5.77 (t, J=6.0 Hz, 1H), 4.41 (dd, J=11.6, 3.2 Hz, 1H), 4.30 (m, 1H), 4.23 (dd, J=12.0, 6.8 Hz, 1H), 2.20 (s, 3H), 2.12 (s, 3H), 2.10 (s, 3H), 2.03 (s, 3H); [M+H]+ 469.4.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washwashed with ethyl acetate (200 mL)
  3. concentrationconcentrated to a yellow solid
  4. additionThe mixture was diluted with H2O (200 mL)
  5. extractionextracted with CH2Cl2 (3×100 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified via Flash chromatography (SiO2, 10% Acetone-CHCl3)

Sources & evidence

ORD record
ord-bbc4c62f816c4d809b70053d0de4de8e
Source dataset
uspto-grants-2011_05
Patent number
US07943759B2

Reaction notes

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