1-(2,3,5,6-Tetra-O-propanoyl-beta-D-glucofuranosyl)uracil → 2,4(1H,3H)-Pyrimidinedione, 1-beta-D-glucofuranosyl-

HRID 1167969Notes

Reaction equation

HRID 1167969 reaction equation
C([O:5][C@@H:6]1[C@@H:10]([O:11]C(=O)CC)[C@@H:9]([C@@H:16]([CH2:22][O:23]C(=O)CC)[O:17]C(=O)CC)[O:8][C@H:7]1[N:28]1[CH:35]=[CH:34][C:32](=[O:33])[NH:31][C:29]1=[O:30])(=O)CC>CO.N>[C@@H:7]1([N:28]2[CH:35]=[CH:34][C:32](=[O:33])[NH:31][C:29]2=[O:30])[O:8][C@H:9]([C@@H:16]([CH2:22][OH:23])[OH:17])[C@H:10]([OH:11])[C@H:6]1[OH:5]

Participants

4

Reactant 1

HCID 700226151-(2,3,5,6-Tetra-O-propanoyl-beta-D-glucofuranosyl)uracil

Product 1

HCID 211411662,4(1H,3H)-Pyrimidinedione, 1-beta-D-glucofuranosyl-Yield 75%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

1-(2,3,5,6-Tetra-O-propanoyl-β-D-glucofuranosyl)uracil was dissolved in methanol saturated with ammonia (15 mL) and left at room temperature overnight. After concentrating in vacuo, the resulting residue was purified by flash silica chromatography, eluting with CHCl3/CH3OH/NH3 aq. (84:15:1), to give 1-βD-glucofuranosyluracil as a colourless solid (680 mg, 75%). A sample was recrystallised from EtOH to give the product as colourless needles, mp 175-176.5° C. (from EtOH), [α]D21=+9.91 (c 1.1 in H2O), (Found: C, 44.0; H, 5.0; N, 10.35. C10H14N2O7 requires C, 43.8; H, 5.15; N, 10.2%); δH (D2O) 7.82 (1H, d, J 8.1, 6-H), 5.79 (1H, d, J 8.1, 5-H), 5.75 (1H, s, 1′-H), 4.27-4.25 (2H, m, 2′- and 3′-H), 4.23 (1H, dd, J 8.6 and 2.7, 4′-H), 4.12 (1H, ddd, J 8.6, 5.4 and 2.7, 5′-H), 3.86 (1H, dd, J 12.1 and 2.7, 6′a-H), 3.37 (1H, dd, J 12.1 and 5.4, 6′b-H); δC (D2O) 166.8 (3-C), 151.9 (2-C), 142.6 (6-C), 101.5 (5-C), 92.4 (1′-C), 82.8 (4′-C), 80.7, 74.7 (2′- and 3′-C), 68.9 (5′-C), 63.8 (6′-C); m/z (FAB) 275.088448 (MH+, C10H15N2O7 requires 275.087926).

Workup

  1. concentrationAfter concentrating in vacuo
  2. customthe resulting residue was purified by flash silica chromatography
  3. washeluting with CHCl3/CH3OH/NH3 aq. (84:15:1)

Sources & evidence

ORD record
ord-5921e811780d46f993560474ae0b606f
Source dataset
uspto-grants-2003_09
Patent number
US06620921B1

Reaction notes

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