Ammonium formate → 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione

HRID 1582426Notes

Reaction equation

HRID 1582426 reaction equation
C([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@:10]1([CH2:25][OH:26])[O:11][C@H:12]2[N:16]1[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]1=[O:18])C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[OH:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@:10]1([CH2:25][OH:26])[O:11][C@H:12]2[N:16]1[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]1=[O:18]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 11121945HCID 11121945, compound

Product 1

HCID 102210801-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedioneYield 84%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of compound (6a) (3 g, 8.4 mmol), 20% Pd(OH)2/C (1.5 g) and ammonium formate (1.6 g) was suspended in 20 mL of methanol. After refluxing the mixture for 10 min, the catalyst was filtered off through celite column and washed by methanol. All the filtrate was combined and concentrated to give a white solid material. The latter was crystallized from 10% ethanol/dichloromethane to yield 1.9 g (84%) of compound (7a) which had the same chromatographic mobility (silica TLC) and H1- and C13-NMR spectra as authentic compound (Koshkin, A. A.; Singh, S. K.; Nielsen, P.; Rajwanshi, V. K.; Kumar, R.; Meldgaard, M.; Olsen, C. E.; Wengel, J., Tetrahedron 1998, 54(14), 3607).

Workup

  1. temperatureAfter refluxing the mixture for 10 min
  2. filtrationthe catalyst was filtered off through celite column
  3. washwashed by methanol
  4. concentrationconcentrated
  5. customto give a white solid material
  6. customThe latter was crystallized from 10% ethanol/dichloromethane

Sources & evidence

ORD record
ord-d78146b04ac145a4b5757882c640f6c2
Source dataset
uspto-grants-2004_05
Patent number
US06734291B2

Reaction notes

Loading…