Ammonium Hydroxide → HCID 10446544, compound

HRID 2210627Notes

Reaction equation

HRID 2210627 reaction equation
C([O:9][C@@H:10]1[C@@H:14]([CH2:15][O:16]C(=O)C2C=CC=CC=2)[O:13][C@@H:12]([N:25]2[CH:32]=[C:31]([C:33](F)(F)F)[C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@@H:11]1[O:37][CH3:38])(=O)C1C=CC=CC=1.[OH-].[NH4+:40]>>[CH3:38][O:37][C@@H:11]1[C@H:10]([OH:9])[C@@H:14]([CH2:15][OH:16])[O:13][C@H:12]1[N:25]1[CH:32]=[C:31]([C:33]#[N:40])[C:29](=[O:30])[NH:28][C:26]1=[O:27]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 10324824HCID 10324824, compound

Product 1

HCID 10446544HCID 10446544, compound

Conditions

Temperature
55 °C

Procedure

3',5'-Di-O-benzoyl-2'-O-methyl-5-trifluoromethyluridine (1.0 g, 2.1 mmoles) was dissolved in concentrated ammonium hydroxide (60 ml) and heated in a sealed tube at 55° C. for 16 hours. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel (30 g) using a gradient of 0-5% methanol in CH2Cl2 to give 0.3 g (50% crude yield) of oil. A small portion of 2'-O-Methyl-5-cyanouridine crystallized from methanol as a slightly impure white solid, mp 208°-211° C. IR (potassium bromide pellet) 2240 cm-1 (sharp, CN); 1H NMR (DMSO-d6): δ3.45(s, 3H, OCH3), 3.5-3.6 (m, 1H, H-5'), 3.7-3.9 (m, 3H, H-3',4',5'), 4.13 (m, 1H, H-2'), 5.17 (d, J=6 Hz, 1H, 3'--OH), 5.48 (br t, 1H, 5'--OH), 5.75 (br s, 1H, H1'), 8.99 (d, J=1.5 Hz, 1H, H-6), 12.08 (br s, 1H, N--H). Anal. Calcd for C11H13N3O6 (283.24): C, 46.64; H, 4.63; N, 14.83. Found: C, 45.98; H, 4.63; N, 14.35.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was chromatographed on silica gel (30 g)
  3. customto give 0.3 g (50% crude yield) of oil
  4. customA small portion of 2'-O-Methyl-5-cyanouridine crystallized from methanol as a slightly impure white solid, mp 208°-211° C

Sources & evidence

ORD record
ord-0f36ecae751e427994d9b5e0433f9e4a
Source dataset
uspto-grants-1995_10
Patent number
US05459243

Reaction notes

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