Ammonium Hydroxide → 2'-O-Methyluridine

HRID 2210628Notes

Reaction equation

HRID 2210628 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]=[CH:31][C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@@H:11]1[O:33][CH3:34])(=O)C1C=CC=CC=1.[OH-].[NH4+]>CO>[CH3:34][O:33][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]=[CH:31][C:29](=[O:30])[NH:28][C:26]1=[O:27]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 21782492HCID 21782492, compound

Product 1

HCID 1022122'-O-MethyluridineYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A sample of 3', 5'-di-O-benzoyl-2'-O-methyl-uridine (0.80 g, 17 mmoles) was deprotected in a mixture of methanol (65 ml) and concentrated ammonium hydroxide (35 ml) overnight at room temperature. The solution was allowed to evaporate to an oil in the fume hood. The residue was triturated with ether (100 ml). The resulting solid was rinsed with ether and dried to afford 0.38 g (86%) of 2'-O-methyluridine as a white solid, mp 158°-159° C. (lit. C. Chavis, ibid., mp 156°-159° C.). (DMSO-d6): δ3.34 (s, 3H, OCH3), 3.5-3.7 (m, 2H, H-5'), 3.7-3.9 (m, 2H, H-3',4'), 4.14 (m, 1H, H-2'), 5.19 (m, 2H, 3',5'--OH), 5.66 (d, J=8 Hz, 1H, H-5), 5.87 (d, J=5 Hz, 1H, H-1'), 7.95 (d, J=8 Hz, 1H, H-6), 11.35 (br s, 1H, N--H). Anal. calcd for C10H14N2O6 (258.23): C, 46.51; H, 5.46; N, 10.85. Found: C, 46.57; H, 5.49; N, 10.82.

Workup

  1. customto evaporate to an oil in the fume hood
  2. customThe residue was triturated with ether (100 ml)
  3. washThe resulting solid was rinsed with ether
  4. customdried

Sources & evidence

ORD record
ord-baf4e3f5416746eeb67b26ba7d118a68
Source dataset
uspto-grants-1995_10
Patent number
US05459243

Reaction notes

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