Ammonium Chloride → HCID 10336476, compound

HRID 2210626Notes

Reaction equation

HRID 2210626 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:36])([F:35])[F:34])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@@H:11]1[O:37][CH3:38])(=O)C1C=CC=CC=1.[Na].[Cl-].[NH4+]>CO>[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]([F:36])([F:34])[F:35])[C:29](=[O:30])[NH:28][C:26]1=[O:27]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 10324824HCID 10324824, compound

Product 1

HCID 10336476HCID 10336476, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3',5'-Di-O-benzoyl-2'-O-methyl-5-trifluoromethyluridine (10.6 g, 20 mmoles) was dissolved in dry methanol (250 ml). Sodium metal (0.7 g, 30 mmoles) was added and the resulting solution was stirred at room temperature for 17 hours. Ammonium chloride (1.6 g, 31 mmoles) was added and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel (100 g) column eluting with a gradient of 0 to 10% methanol in CH2Cl2 to afford 6.1 g (94%) 2'-O-methyl-5-trifluoromethyluridine as a white solid, mp 192°-194°. 1H NMR (DMSO-d6): δ3.43 (s, 3H, OCH3), 3.5-3.8 (m, 2H, H-5'), 3.8-4.0 (m, 2H, H-3',4'), 4.12 (m, 1H, H-2'), 5.18 (d, J=7 Hz, 1H, 3' -OH), 5.40 (br t, 1H, 5'-OH), 5.78 (d, J=2.5 Hz, 1H-1'), 8.92 (s, 1H, H-6), 11.80 (br s, 1H, N-H). Anal. Calcd for C11H13F3N2O6 (326.23): C, 40.49; H, 3.99; N, 8.59. Found: C, 40.42; H, 4.17; N, 8.32.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was chromatographed on a silica gel (100 g) column
  3. washeluting with a gradient of 0 to 10% methanol in CH2Cl2

Sources & evidence

ORD record
ord-ce13a1b8daa24356820f5e6edf807863
Source dataset
uspto-grants-1995_10
Patent number
US05459243

Reaction notes

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